Updated on 2021/12/21

写真a

 
KUROBOSHI Manabu
 
Organization
Faculty of Natural Science and Technology Associate Professor
Position
Associate Professor
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Degree

  • Mr. of Engineering ( Kyoto University )

  • Dr. of Engineering ( Kyoto University )

Research Interests

  • 有機電気化学

  • 有機金属化学

  • Electroorganic Chemistry

  • Organometallic Chemistry

Research Areas

  • Nanotechnology/Materials / Synthetic organic chemistry

Professional Memberships

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Committee Memberships

  • 有機電気化学研究会   幹事  

    2009 - 2010   

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    Committee type:Academic society

    有機電気化学研究会

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  • 日本化学会   座長  

    2009   

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    Committee type:Academic society

    日本化学会

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  • 有機電子移動化学討論会   座長  

    2009   

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    Committee type:Academic society

    有機電子移動化学討論会

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  • 電気化学会   座長  

    2009   

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    Committee type:Academic society

    電気化学会

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  • 有機電気化学研究会   幹事  

    2008   

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    Committee type:Academic society

    有機電気化学研究会

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Papers

  • Nucleophilic Substitution of 2,2-Bis(arylthio)-4,4,6,6-tetrachlorocyclotriphosphazene with Ammonia, Phenoxide, and Thiophenoxide Reviewed

    Manabu Kuroboshi,* Ayako Ueno, Ayane Kawano, and Hideo Tanaka

    heterocycles   104   69 - 84   2022.1

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    Language:English   Publishing type:Research paper (scientific journal)  

  • New and Practical Applications of Functionalized Cyclotriphosphazene Core-Based Materials Reviewed

    Manabu Kuroboshi* and Hideo Tanaka

    heterocycles   100   1513 - 1578   2020

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  • Synthesis of Arylthiochlorocyclotriphosphazenes Reviewed

    Manabu Kuroboshi,* Masaki Mikasa, and Hideo Tanaka

    heterocycles   98   940 - 953   2019

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  • Electrooxidation of Chlorodiphenylphosphine under Ammonia Atmosphere. Synthesis of 2,2,4,4,6,6-Hexaphenylcyclotriphosphazene and Iminobis(aminodiphenylphosphorus) Chloride Reviewed

    Manabu Kuroboshi,* Yasunari Masumoto, and Hideo Tanaka

    heterocycles   98   1258 - 1264   2019

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  • Synthesis of Aminated Cyclotriphosphazenes. Solvent Effects on the Product-Selectivity of the Amination Reviewed

    Manabu Kuroboshi,* Masahiko Morita, Yasunari Masumoto, Masaki Mikasa, Ryohei Toza, and Hideo Tanaka

    heterocycles   98   931 - 939   2019

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  • Reduction of phosphine oxides to the corresponding phosphine derivatives in Mg/Me3SiCl/DMI system Reviewed

    Manabu Kuroboshi, Toshihito Kita, Asuka Aono, Toshimasa Katagiri, Seiya Kikuchi, Syoko Yamane, Hiromu Kawakubo, Hideo Tanaka

    TETRAHEDRON LETTERS   56 ( 7 )   918 - 920   2015.2

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:PERGAMON-ELSEVIER SCIENCE LTD  

    Direct reductions of phosphine oxides to the corresponding phosphines were performed successfully by using Mg/Me3SiCl/DMI system. The reduction proceeded under mild conditions and was applicable to a wide range of phosphine oxides; triarylphosphine oxides, alkyldiarylphosphine oxides, and dialkylarylphosphine oxides gave the corresponding phosphines in good to excellent yields. (C) 2015 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2014.12.132

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  • DIQUAT DERIVATIVES, A PRECURSOR OF ORGANIC REDUCTANT Reviewed

    Manabu Kuroboshi, Takashi Kondo, Hideo Tanaka

    HETEROCYCLES   90 ( 1 )   723 - 729   2015.1

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    Electroreduction of diquat triflate gave a potent organic reductant, which promoted reductive dimerization of aryl bromides in the presence of palladium catalysts to give the corresponding biaryl compounds.
    This manuscript is dedicated to the celebration of the 77th birthday of Prof. Isao Kuwajima, Professor emeritus of Tokyo Institute of Technology.

    DOI: 10.3987/COM-14-S(K)53

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  • FACILE SYNTHESIS OF DIETHYL AZODICARBOXYLATE AND DIETHYLHYDRAZODICARBOXYLATE VIA THE SEQUENTIAL BROMINATION AND HOFMANN-TYPE REARRANGEMENT OF ETHYLALLOPHANATE Reviewed

    Hiromu Kawakubo, Tomoko Suzuki, Kazutaka Nishino, Futaba Hara, Tomoyoshi Takano, Yoshito Takebayashi, Masato Onodera, Aya Mitsui, Haruka Yahagi, Hiroyuki Takayama, Manabu Kuroboshi, Hideo Tanaka

    SYNTHETIC COMMUNICATIONS   45 ( 9 )   1068 - 1072   2015

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:TAYLOR & FRANCIS INC  

    Diethyl azodicarboxylate (DEAD) is a well-known coupling reagent that can be readily synthesized from diethylhydrazodicarboxylate (DEHD). The bromination of commercially available ethyl allophanate (1) in CHCl3, followed by the Hofmann-type rearrangement reaction of the resulting N-brominated species 2 and 3 in C2H5OH in the presence of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), gave DEHD in good yield from a one-pot process. Interestingly, however, the bromination and Hofmann-type rearrangement reactions did not occur in the presence of N(C2H5)(3). These results therefore suggest that this reaction is reliant upon a high level of reactivity during the bromination reaction to give 2 and 3, and that these N-brominated species require the presence of a strong and nonnucleophilic base to undergo the Hofmann-type rearrangement to give DEHD.

    DOI: 10.1080/00397911.2014.1002137

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  • Electroreduction of tetra-coordinate phosphonium derivatives; one-pot transformation of triphenylphosphine oxide into triphenylphosphine Reviewed

    Manabu Kuroboshi, Tomotake Yano, Shogo Kamenoue, Hiromu Kawakubo, Hideo Tanaka

    TETRAHEDRON   67 ( 32 )   5825 - 5831   2011.8

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    Electroreduction of triphenylphosphine dichloride in acetonitrile was performed successfully in an undivided cell fitted with an aluminium sacrificial anode and a platinum cathode, wherein Al(3+), which was electrogenerated at the anode would react as a Lewis acid with triphenylphosphine dichloride to afford tetra-coordinate chlorotriphenylphosphonium species and subsequent two-electron reduction at the cathode would give triphenylphosphine. One-pot transformation of triphenylphosphine oxide to triphenylphosphine was achieved successfully by the treatment of triphenylphosphine oxide with oxalyl chloride and subsequent electroreduction. In a similar manner, some tetra-coordinate triphenylphosphonium species derived from triphenylphosphine oxide were reduced electrochemically to triphenylphosphine in moderate yields. (C) 2011 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2011.05.044

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  • Electrooxidative Glycosylation Through C—S Bond Cleavage of 1-Arylthio-2,3-dideoxyglycosides. Synthesis of 2′,3′-Dideoxynucleosides. Reviewed

    Koichi Mitsudo, Takashi Kawaguchi, Seiji Miyahara, Wataru Matsuda, Manabu Kuroboshi, Hideo Tanaka

    ChemInform   37 ( 9 )   2006.2

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    DOI: 10.1002/chin.200609212

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  • TRIS(DIALKYLAMINO)SULFONIUM DIFLUOROTRIMETHYLSILICATE Reviewed

    M KUROBOSHI, T HIYAMA

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   48 ( 11 )   1050 - 1051   1990.11

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    Language:Japanese   Publishing type:Research paper (scientific journal)   Publisher:SOC SYNTHETIC ORGANIC CHEM JPN  

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MISC

  • SYNTHESIS OF DENDRIMER-TYPE VIOLOGEN AND ITS USE IN Pd-MEDIATED HOMOCOUPLING OF ARYL HALIDES

    Manabu Kuroboshi, Atsuki Kojima, Hideo Tanaka

    HETEROCYCLES   94 ( 11 )   2132 - 2140   2017.11

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    Dendrimer-type viologen (V2+D.) was prepared from mesitylene and 4,4'-bipyridyl. Electroreduction of V2+D. gave the corresponding quinoid (V-0.D.), which promoted Pd-catalyzed homocoupling of aryl bromides Ar-Br to give the corresponding biaryls Ar-Ar in moderate to good yields.

    DOI: 10.3987/COM-17-13812

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  • Viologen as catalytic organic reductant: electro-reductive dimerization of aryl bromides in a Pd/viologen double mediatory system

    Manabu Kuroboshi, Takuya Shiba, Hideo Tanaka

    TETRAHEDRON LETTERS   54 ( 28 )   3666 - 3668   2013.7

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    Viologen can be used as an in situ recyclable organic reductant Pd-catalyzed electrochemical reductive coupling of aryl bromides was performed by using a catalytic amount of viologen to afford the corresponding biaryls in good to moderate yields. (C) 2013 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2013.04.127

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  • Electro-reductive Homo-Coupling Reaction of Aryl Bromides in PdCl2(PPh3)(2)/Pyridinium Salt Double Mediatory Systems

    Hideo Tanaka, Manabu Kuroboshi, Ryukei Kataoka, Ryosuke Suzuki

    ELECTROCHEMISTRY   81 ( 5 )   356 - 358   2013.5

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    Electro-reductive homo-coupling of aryl bromides in a double mediatory system involving catalytic amounts of PdCl2(PPh3)(2) and N-alkyl-4-alkoxycarbonylpyridiniunn salts was performed successfully to afford the corresponding biaryls in good to moderate yields. (C) The Electrochemical Society of Japan, All rights reserved.

    DOI: 10.5796/electrochemistry.81.356

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  • Electroreduction of aryl halides loaded on palladium-immobilized activated carbon

    Manabu Kuroboshi, Hiroaki Idei, Naoaki Hara, Yuta Kokui, Hideo Tanaka

    Electrochemistry   81 ( 5 )   359 - 361   2013.5

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    Electroreduction of aryl halides loaded on the Pd-immobilized activated carbon and/or activated carbon cloth proceeded smoothly by using a newly designed stacked-type cell to give the corresponding dehalogenated arenes.

    DOI: 10.5796/electrochemistry.81.359

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  • Amphiphilic viologen: Electrochemical generation of organic reductant and pd-catalyzed reductive coupling of aryl halides in water

    Manabu Kuroboshi, Takashi Yamamoto, Hideo Tanaka

    Synlett   24 ( 2 )   197 - 200   2013

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    Electroreduction of 1,1′-bis(methoxyethoxyethoxyethyl)-4,4′- bipyridinium tosylate generated amphiphilic organic reductants, which promoted the Pd-catalyzed reductive coupling of aryl bromides in water to give the corresponding biaryls. The yields and selectivity of biaryls depended on the length of ethyleneoxy groups and substituents of the aryl bromides. © Georg Thieme Verlag Stuttgart · New York.

    DOI: 10.1055/s-0032-1317857

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  • Electroreduction of Triphenylphosphine Oxide to Triphenylphosphine in the Presence of Chlorotrimethylsilane

    Hiromu Kawakubo, Manabu Kuroboshi, Tomotake Yano, Kazuma Kobayashi, Syogo Kamenoue, Tomomi Akagi, Hideo Tanaka

    SYNTHESIS-STUTTGART   ( 24 )   4091 - 4098   2011.12

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    Electroreduction of triphenylphosphine oxide to triphenylphosphine in an acetonitrile solution of tetrabutylammonium bromide in the presence of chlorotrimethylsilane was performed successfully in an undivided cell fitted with a zinc anode and a platinum cathode under constant current. A plausible mechanism involving, (1) one-electron reduction of triphenylphosphine oxide generating the corresponding anion radical [Ph(3)P(center dot)-O(-)], (2) subsequent reaction with chlorotrimethylsilane affording the (trimethylsiloxy)triphenylphosphorus radical [Ph(3)P(center dot)-OSiMe(3)], and (3) further one-electron reduction followed by P-O bond fission leading to triphenylphosphine is proposed. In a similar manner, electroreduction of some triarylphosphine oxides and alkyldiarylphosphine oxides was executed to give the corresponding phosphine derivatives in good to moderate yields.

    DOI: 10.1055/s-0031-1289612

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  • A Practical One-Pot Transformation of Triphenylphosphine Oxide to Triphenylphosphine by Reduction of in situ Generated Triphenylphosphine Dichloride

    Tomotake Yano, Masakatsu Hoshino, Manabu Kuroboshi, Hideo Tanaka

    SYNLETT   ( 5 )   801 - 803   2010.3

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    One-pot transformation of triphenylphosphine oxide to triphenylphosphine was achieved by the reaction of triphenylphosphine oxide with oxalyl chloride, which led to the formation of triphenylphosphine dichloride, and subsequent reduction of triphenylphosphine dichloride with a combination of aluminum-catalytic metal salt.

    DOI: 10.1055/s-0029-1219194

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  • Electroreduction of triphenylphosphine dichloride and the efficient one-pot reductive conversion of phosphine oxide to triphenylphosphine

    Tomotake Yano, Manabu Kuroboshi, Hideo Tanaka

    TETRAHEDRON LETTERS   51 ( 4 )   698 - 701   2010.1

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    Electroreduction of triphenylphosphine dichloride in acetonitrile was performed successfully in an undivided cell fitted with an aluminium sacrificial anode and a platinum cathode. Further, the one-pot transformation of triphenylphosphine oxide to triphenylphosphine was achieved successfully by the treatment of triphenylphosphine oxide in acetonitrile with oxalyl chloride and subsequent electrochemical reduction. (C) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2009.11.115

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  • Design of Redox-Mediatory Systems for Electro-Organic Synthesis

    Hideo Tanaka, Manabu Kuroboshi, Koichi Mitsudo

    ELECTROCHEMISTRY   77 ( 12 )   1002 - 1009   2009.12

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    Halide ion-promoted desulfo-halogenation was applied successfully to synthesis of 4-chloro-2-azetidinone 1, a potent intermediate for carbapenem synthesis. and stereoselective N-glycosylation of 2,3-deoxyglycosides. Bromide ion/N-oxyl compounds (TEMPO) double mediatory systems enabled us to develop several aqueous electrolysis media free from organic solvents, e.g., silica gel or polymer particles/water disperse systems and water-soluble TEMPO-mediated oil-in-water emulsion systems, in which electrooxidation of alcohols was carried out successfully in a simple beaker-type undivided cell under a constant current condition. Notably, the work-up process was very simple and the solid particles (disperse phase) and the aqueous solutions (disperse media) were easily recovered and reused, offering a totally closed system. In Pd(OAc)(2)/TEMPO double mediatory systems, electrogeneration of active cationic palladium catalysts was integrated into electrooxidative Wacker-type reaction. In a similar manner, Wacker-type cyclization and homo-coupling of arylboronic acids were successfully achieved.

    DOI: 10.5796/electrochemistry.77.1002

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  • Chemo- and Product-selective Electrooxidation of 3-(Arylthiomethyl)-Delta(3)-cephems

    Hideo Tanaka, Yoshihisa Tokumaru, Ken-ichi Fukui, Manabu Kuroboshi, Sigeru Torii, Anny Jutand, Christian Amatore

    SYNTHESIS-STUTTGART   ( 20 )   3449 - 3459   2009.10

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    Electrolysis of 3-arylthiomethyl-Delta(3)-cephems possessing various substituents on the arylthio moiety undergo chemoselective and product-selective electrooxidation to give several different products. These include isomeric mixtures of the corresponding methoxylated cephems, a bis[(Delta(3)-cephem-3-yl)methyl]disulfide or a 3-dimethoxymethyl-Delta(3)-cephem. The selectivity of the oxidation is highly dependent on the nature of the substituents on the arylthio moiety which suggests that both steric and electronic effects play an important role in the electrooxidation 3-arylthiomethyl-Delta(3)-cephems.

    DOI: 10.1055/s-0029-1216972

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  • Electroorganic synthesis in oil-in-water (O/W) nanoemulsion: TEMPO-mediated electrooxidation of amphiphilic alcohols in water

    Manabu Kuroboshi, Tomonori Yoshida, Jun Oshitani, Kuniaki Goto, Hideo Tanaka

    TETRAHEDRON   65 ( 34 )   7177 - 7185   2009.8

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    Oil-in-water nanoemulsion which consisted of TEMPO, amphiphilic alcohols, and water offered unique reaction environments for electrooxidation of the alcohols to give the corresponding carboxylic acids in good to excellent yields. (c) 2009 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2009.06.005

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  • Electrooxidation of Alcohols in N-Oxyl-Immobilized Silica Gel/Water Disperse System: Approach to Totally Closed System

    Manabu Kuroboshi, Kentaro Goto, Hideo Tanaka

    SYNTHESIS-STUTTGART   ( 6 )   903 - 908   2009.3

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    Electrooxidation of-alcohols in a disperse system with N-oxyl-immobilized silica gel as a disperse phase and an aqueous NaBr/NaHCO(3) solution as a disperse medium proceeded smoothly to give the corresponding carbonyl compounds. The N-oxyl-immobilized silica gel 1 was prepared by silane-coupling method. Recycling of both the aqueous Solution and the N-oxyl-immobilized silica gel 1 was performed successfully.

    DOI: 10.1055/s-0028-1087987

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  • Electroreductive Generation of Recyclable Organic Reductant from N,N '-Dioctyl-4,4'-bipyridinium and Pd-Catalyzed Reductive Coupling of Aryl Halides

    Manabu Kuroboshi, Ryoto Kobayashi, Takayuki Nakagawa, Hideo Tanaka

    SYNLETT   ( 1 )   85 - 88   2009.1

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    Electroreduction of N,N'-dioctyl-4,4'-bipyridinium bis(tri-flimide) [C(8)V(2+)][Tf(2)N(-)](2) in THF gave a dark blue solution of the corresponding quinoid C(8)V(0), which worked as an efficient organic reductant for Pd-catalyzed reductive coupling of aryl bromides to give the corresponding biphenyl derivatives in good yields. After usual workup, [C(8)V(2+)][Tf(2)N(-)](2) was recovered and reused for generation of the organic reductant C(8)V(0).

    DOI: 10.1055/s-2008-1087386

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  • Development of aqueous media for electroorganic synthesis.

    Tanaka, Hideo, Kuroboshi, Manabu

    Kagaku to Kogyo   83 ( 5 )   206 - 214   2009

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  • Recyclable Electron Transfer System: Electroreduction of Viologen in Ionic Liquids and Pd-catalyzed Reductive Coupling of Aryl Halides

    Manabu Kuroboshi, Akiko Kuwano, Hideo Tanaka

    ELECTROCHEMISTRY   76 ( 12 )   862 - 864   2008.12

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    Electroreduction of N,N'-dioctyl-4,4'-bipyridinium (C8V2+) bis(triflimide) was carried out in ionic liquids to give the corresponding quinoid C8V0, which promoted reductive coupling of aryl halides in the presence of a Pd catalyst to give biaryls. C8V2+ and the ionic liquids were used repeatedly.

    DOI: 10.5796/electrochemistry.76.862

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  • ELECTROOXIDATIVE DESULFURIZATION/CHLORINATION. A FACILE SYNTHESIS OF 4-CHLORO-2-AZETIDINONES, A POTENT INTERMEDIATE FOR CARBAPENEMS

    Manabu Kuroboshi, Masayoshi Miyada, Syoichi Tateyama, Hideo Tanaka

    HETEROCYCLES   76 ( 2 )   1471 - 1484   2008.11

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    (3S,4R)-3-(1'(R)-tert-Butyldimethylsilyloxyethyl)-4-chloro-2-azetidinone (2), a potent intermediate for the synthesis of carbapenem antibiotics, was synthesized by thermal ring opening/acylation of (3S,5R,6S)-6-(1'(R)-tert-butyldimethylsilyloxyethyl)penicillanate S-oxide (8) leading to 4-acylthio-2-azetidinone derivative 9 and subsequent removal of the N-substituent followed by electrooxidative desulfurization/chlorination of the C(4)-acylthio moiety.

    DOI: 10.3987/COM-08-S(N)110

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  • Diastereoselective synthesis of 6-bromo-6-(1-hydroxyethyl)penicillanate by cross-coupling of 6,6-dibromopenicillanate and acetaldehyde promoted with grignard reagents: Role of amine ligands

    Manabu Kuroboshi, Keiko Mesaki, Syoichi Tateyama, Hideo Tanaka

    HETEROCYCLES   73 ( 1 )   877 - +   2007.12

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    Grignard reagent-promoted coupling reaction of diphenylmethyl 6,6-dibromopenicillanate 1b with acetaldehyde in the presence of N,N,N',N",N"-pentamethyldiethylenetriamine took place in a highly diastereoselective manner to give diphenylmethyl (1'R,3S,5R,6S)-6-bromo-6-(1'-hydroxyethyl)penicillanate 2b effectively, which is a potent intermediate for the synthesis of carbapenem antibiotics.

    DOI: 10.3987/COM-07-S(U)47

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  • Electroorganic synthesis in oil-in-water nanoemulsion: TEMPO-mediated electrooxidation of amphiphilic alcohols in water

    Tomonori Yoshida, Manabu Kuroboshi, Jun Oshitani, Kuniaki Gotoh, Hideo Tanaka

    SYNLETT   in press ( 17 )   2691 - 2694   2007.10

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    Oil-in-water nanoemulsions, consisting of TEMPO, amphiphilic alcohols, and water, offer unique reaction environments for electrooxidation of the alcohols to give the corresponding carboxylic acids in good to excellent yields.

    DOI: 10.1055/s-2007-991070

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  • Electrooxidation of alcohols in an N-oxyl-immobilized rigid network polymer particles/water disperse system

    J Kubota, T Ido, M Kuroboshi, H Tanaka, T Uchida, K Shimamura

    TETRAHEDRON   62 ( 20 )   4769 - 4773   2006.5

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    The electrooxidation of alcohols in an aqueous disperse system with N-oxyl-immobilized poly(p-phenylene benzobisthiazole) network polymer particles (PBZT(NT)-N-Oxyl) as a disperse phase was performed successfully in a simple beaker-type undivided cell tinder a constant current condition to afford the corresponding ketones, aldehydes, and/or carboxylic acid in moderate to good yields. Recycle use of both the PBZT(NT)-N-Oxyl particles and the aqueous media could be achieved successfully by immobilization of additional N-oxyl moiety on the polymer particles in an appropriate interval. Notably, the shape and the particle size of PBZT(NT)-N-Oxyl were not appreciably changed even after 60 times recycle use. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2006.03.020

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  • Electrooxidative N-Halogenation of 2-Azetidinone Derivatives

    Tanaka, H, Arai, S, Ishitobi, Y, Kuroboshi, M, Torii, S

    Electrochemistry   2006

  • Electrooxidation of alcohols in an N-oxyl-immobilized poly(ethylene-co-acrylic acid)/water disperse system

    H Tanaka, J Kubota, S Miyahara, M Kuroboshi

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   78 ( 9 )   1677 - 1684   2005.9

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    Language:English   Publisher:CHEMICAL SOC JAPAN  

    The electrooxidation of alcohols in a disperse system with N-oxyl-immobilized polymer particles (PE-co-AA-N-Oxyl), prepared from poly(ethylene-co-acrylic acid) (PE-co-AA-Co2H), as a disperse phase and an aqueous saturated NaHCO3 containing 20 wt % NaBr as a disperse medium was successfully performed in a simple beaker-type undivided cell under constant-current conditions. The electrooxidation of alcohols proceeded in a similar manner by the use of PEco-AA-CO2H as a disperse phase, though the current efficiency decreased in some extent. Protection of most of the carboxylic acid moieties on the surface of PE-co-AA-CO2H by esterification or amidation resulted in significant decrease of the product yields, suggesting that the carboxylic acid moieties on the surface of PE-co-AA-CO2H would also act as a mediator for the electrooxidation of alcohols. Both the recovered PE-co-AA-N-Oxyl and the aqueous solution were used repeatedly for the electrooxidation of alcohols, thereby offering a formally closed system for the electrooxidation of alcohols.

    DOI: 10.1246/bcsj.78.1677

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  • Reductive Coupling of Aryl Bromides Using Cat. Pd/TDAE System in Ionic Liquids

    M. Kuroboshi, T. Takeda, R. Motoki, H. Tanaka

    Chem. Lett.   2005

  • Electrooxidative Glycosylation through C-S Bond Cleavage of 1-Arylthio-2,3-dideoxyglycosides. Synthesis of 2',3'-Dideoxynucleosides

    K. Mitsudo, T. Kawaguchi, S. Miyahara, W. Matsuda, M. Kuroboshi, H. Tanaka

    Org. Lett.   2005

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  • The oxidation of alcohols in N-oxyl-immobilized silica gel/aqueous NaOCl disperse systems. A prominent access to a column-flow system

    H Tanaka, JY Chou, M Mine, M Kuroboshi

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   77 ( 9 )   1745 - 1755   2004.9

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    Language:English   Publishing type:Book review, literature introduction, etc.   Publisher:CHEMICAL SOC JAPAN  

    The oxidation of alcohols was performed successfully in a disperse system with N-oxyl-adsorbed or immobilized silica gel as a disperse phase and aqueous NaOCl as a disperse medium. In the disperse system, the oxidation of sec-alcohols afforded the corresponding ketones, while prim-alcohols were oxidized to aldehydes and/or carboxylic acids depending on their structures and reaction conditions. The N-oxyl-immobilized silica gel was recovered and repeatedly used without a significant change in the product yields. A column-flow system was also investigated for the oxidation of alcohols by use of a newly devised column packed with the N-oxyl-immobilized silica gel.

    DOI: 10.1246/bcsj.77.1745

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  • N-Oxyl-mediated electrooxidation in ionic liquid. A prominent approach to totally closed system.

    Kuroboshi, Manabu, Fujisawa, Junko, Tanaka, Hideo

    Electrochemistry (Tokyo, Japan)   2004

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  • Aluminium as an electron pool for organic synthesis. Multi-metal redox-promoted reactions.

    Tanaka, Hideo, Kuroboshi, Manabu

    Current Organic Chemistry   (2004), 8(11), 1027-1056.   2004

  • Electro-oxidation of alcohols in N-oxyl-immobilized ionic liquids . approach to a totally closed system.

    Kuroboshi, Manabu, Fujisawa, Junko, Tanaka, Hideo

    Proceedings - Electrochemical Society (2004), 2004-10(Analytical, Mechanistic, and Synthetic Organic Electrochemistry),   2004

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  • Water/fine particle dispersed aqueous electrolytic synthesis.

    Tanaka, Hideo, Kuroboshi, Manabu

    Yuki Denkai Gosei no Shintenkai   2004

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  • Palladium-catalyzed tetrakis(dimethylamino)ethylene-promoted reductive coupling of aryl halides

    M Kuroboshi, Y Waki, H Tanaka

    JOURNAL OF ORGANIC CHEMISTRY   68 ( 10 )   3938 - 3942   2003.5

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    Tetrakis(dimethylamino)ethylene (TDAE)/cat. PdCl2(PhCN)(2)-promoted reductive coupling of aryl bromides having either electron-donating or electron-withdrawing groups on their para- and/or meta-position proceeded smoothly to afford the corresponding biaryls in good to excellent yields. Notably, TDAE is such a mild reductant that easily reducible groups, such as carbonyl and nitro groups, are tolerate. A similar reductive coupling of ortho-substituted aryl bromides did not occur at all. The proper choice of palladium catalysts is essential for the reductive coupling; thus, PdCl2(PhCN)(2), PdCl2(MeCN)(2), Pd(hfacac)(2), Pd-2(dba)(3), PdCl2, and Pd(OAc)(2) were used successively for this reaction, but phosphine-ligated palladium catalysts such as Pd(PPh3)(4), PdCl2(PPh3)(2), and Pd(dppp) did not promote the reaction. The reductive coupling did not occur with nickel catalysts such as NiBr2, NiCl2(bpy), and Ni(acac)(2). The TDAE/cat. palladium-promoted reductive coupling of aryl halides having electron-withdrawing groups took place more efficiently than that of aryl halides substituted with electron-donating groups. A plausible mechanism of TDAE/cat. palladium-promoted reaction is discussed.

    DOI: 10.1021/jo0207473

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  • Asymmetric dihydroxylation of olefins in a chiral ligand-immobilized silica-gel/water disperse system

    Kuroboshi Manabu, Mizone Toshiki, Tanaka Hideo

    Proceedings - Electrochemical Society (2003), 2003-12(Mechanistic and Synthetic Aspects of Organic and Biological Electrochemistry)   2003

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  • Electrooxidation of alcohols in an N-oxyl immobilized rigid polymer particles disperse water system

    Tanaka Hideo, Ido ohru, Kubota Jun, Kuroboshi Manabu, Uchida Tetsuya, Shimamura Kaoru

    Proceedings - Electrochemical Society (2003), 2003-12(Mechanistic and Synthetic Aspects of Organic and Biological Electrochemistry   2003

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  • Electrooxidation of alcohols in a disperse system with N-oxyl-immobilized polyethylene particles as disperse phase and aqueous NaHCO3/NaBr as disperse media. A totally closed electrolysis system

    田中秀雄, 久保田潤, 糸川真司, 井戸 亨, 黒星, 学, 島村, 薫, 内田哲也

    Synlett   2003

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  • Tetrakis(dimethylamino)ethylene (TDAE)-Pd promoted reductive homocoupling of aryl halides

    M Kuroboshi, Y Waki, H Tanaka

    SYNLETT   ( 4 )   637 - 639   2002.4

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    A combination of tetrakis(dimethylamino)ethylene (TDAE) and palladium catalysts promoted reductive homo-coupling of aryl halides efficiently to afford the corresponding biaryls in good to quantitative yields. TDAE acted as a very mild reductant, and easily reducible functional groups, such as a nitro, formyl, ester, or nitrite group, remained unchanged.

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  • 繰り返し何度でも使える高性能な不斉触媒を目指して

    黒星 学

    化学   2002

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  • Substitution vs. addition. Regioselective electrobromination of benzofuran

    H Tanaka, Y Kawakami, M Kuroboshi, S Torii

    HETEROCYCLES   54 ( 2 )   825 - +   2001.2

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    Regioselective electro-bromination of benzofuran (2) was achieved successfully by an adequate choice of solvents and bromide salts to afford 5-bromobenzofuran (1), 5,7-dibromobenzofuran (3), and 2,3-dibromo-2,3-dihydrobenzofuran (4), respectively. Upon electrolysis of benzofuran (2) in AcOH/H2O (100/1) containing NH4Br, substitution at the C(5)-position of benzofuran (2) proceeded smoothly to afford 5-bromobenzofuran (1). After passage of totally 4 F/mol of electricity in a similar medium, 5,7-dibromobenzofuran (3) was obtained as a sole product. On the other hand, electrolysis of benzofuran (2) in CH2Cl2/H2O (1/1) and/or AcOH/H2O (10/1) in the presence of either NaBr or NH4Br afforded 2,3-dibromo-2,3-dihydrobenzofuran (4), exclusively.

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  • Oxidative Desulfurization-Fluorination: A Facile Entry to a Wide Variety of Organofluorine Compounds Leading to Novel Liquid-Crystalline Materials

    M. Kuroboshi, K. Kanie, T. Hiyama

    Adv. Synth. Catal.   343 (3), 235-250 (2001)   2001

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  • Dimethyl(phenyl)silane

    T. Hiyama, M. Kuroboshi

    e-EROS Encyclopedia of Reagents for Organic Synthesis   2001

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  • 1,1-Dibromo-2-ethoxycyclopropane

    T. Hiyama, M. Kuroboshi

    e-EROS Encyclopedia of Reagents for Organic Synthesis   2001

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  • 3-Chloro-3-methyl-2-trimethylsilyloxy-1-butene

    T. Hiyama, M. Kuroboshi

    e-EROS Encyclopedia of Reagents for Organic Synthesis   2001

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  • An Aqueous Silica Gel Disperse Electrolysis System. N-Oxyl-Mediated Electrooxidation of Alcohols

    H. Tanaka, Y. Kawakami, K. Goto, M. Kuroboshi

    Tetrahedron Lett.   2001

  • Electrochemical Asymmetric Epoxidation of Olefins by Using An Optically Active Mn-Salen Complex

    H. Tanaka, M. Kuroboshi, H. Takeda, H. Kanda, S. Torii

    J. Electroanal. Chem.   2001

  • Oxidative desulfurization-fluorination - Facile synthesis of organofluorine compounds and development of fluorine-containing novel liquid-crystalline materials

    K Kanie, M Kuroboshi, T Hiyama

    NIPPON KAGAKU KAISHI   ( 11 )   749 - 761   2000.11

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    Language:Japanese   Publishing type:Book review, literature introduction, etc.   Publisher:CHEMICAL SOC JAPAN  

    The oxidative desulfurization-fluorination reaction of organosulfur compounds using an N-halo imide and a fluoride source is demonstrated to be an effective and mild fluorination method that allows to synthesize various types of organofluorine compounds containing a difluoromethylene unit, tri fluoromethyl-substituted aromatics, trifluoromethyl ethers, and N-trifiuoromethylamines in high yields with high chemoselectivity. Herein briefly summarized are the synthetic procedures for such organofluorine compounds and scope and limitations of the reaction. The reaction is applied to the synthesis of novel liquid-crystalline materials having a fluorine functional group such as an N-trifluoromethylamino, trifluoromethoxy, or 1,2-difluoroethylene group. The fluorine-containing liquid-crystalline materials are compared with the corresponding non-fluorinated materials in respect to phase transition behaviors and electro-optical properties. The novel fluorine-containing liquid crystals are shown to be suitable for not only super twisted nematic (STN) but also thin film transistor (TFT) -addressed liquid crystal displays.

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  • Electro-oxidative kinetic resolution of sec-alcohols by using an optically active N-oxyl mediator

    Manabu Kuroboshi, Hiroshi Yoshihisa, Mariana N. Cortona, Yusuke Kawakami, Zake Gao, Hideo Tanaka

    Tetrahedron Letters   41 ( 42 )   8131 - 8135   2000.10

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    Electro-oxidative kinetic resolution of sec-alcohols mediated with a catalytic amount of an optically active N-oxyl was performed by use of a simple undivided cell under constant current conditions. The selectivity factor (S-value) increased remarkably when the reaction was performed at lower temperatures. The optically active N-oxyl was recovered and used repeatedly without any change in efficiency and selectivity. © 2000 Elsevier Science Ltd.

    DOI: 10.1016/S0040-4039(00)01419-2

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  • Electro-oxidative kinetic resolution of sec-alcohols by using an optically active N-oxyl mediator

    Manabu Kuroboshi, Hiroshi Yoshihisa, Mariana N. Cortona, Yusuke Kawakami, Zake Gao, Hideo Tanaka

    Tetrahedron Letters   41 ( 42 )   8131 - 8135   2000.10

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    Electro-oxidative kinetic resolution of sec-alcohols mediated with a catalytic amount of an optically active N-oxyl was performed by use of a simple undivided cell under constant current conditions. The selectivity factor (S-value) increased remarkably when the reaction was performed at lower temperatures. The optically active N-oxyl was recovered and used repeatedly without any change in efficiency and selectivity. © 2000 Elsevier Science Ltd.

    DOI: 10.1016/S0040-4039(00)01419-2

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  • Electro-oxidative kinetic resolution of sec-alcohols by using an optically active N-oxyl mediator

    Manabu Kuroboshi, Hiroshi Yoshihisa, Mariana N. Cortona, Yusuke Kawakami, Zake Gao, Hideo Tanaka

    Tetrahedron Letters   41 ( 42 )   8131 - 8135   2000.10

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    Electro-oxidative kinetic resolution of sec-alcohols mediated with a catalytic amount of an optically active N-oxyl was performed by use of a simple undivided cell under constant current conditions. The selectivity factor (S-value) increased remarkably when the reaction was performed at lower temperatures. The optically active N-oxyl was recovered and used repeatedly without any change in efficiency and selectivity. © 2000 Elsevier Science Ltd.

    DOI: 10.1016/S0040-4039(00)01419-2

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  • Electro-oxidative kinetic resolution of sec-alcohols by using an optically active N-oxyl mediator

    Manabu Kuroboshi, Hiroshi Yoshihisa, Mariana N. Cortona, Yusuke Kawakami, Zake Gao, Hideo Tanaka

    Tetrahedron Letters   41 ( 42 )   8131 - 8135   2000.10

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    Language:English  

    Electro-oxidative kinetic resolution of sec-alcohols mediated with a catalytic amount of an optically active N-oxyl was performed by use of a simple undivided cell under constant current conditions. The selectivity factor (S-value) increased remarkably when the reaction was performed at lower temperatures. The optically active N-oxyl was recovered and used repeatedly without any change in efficiency and selectivity. © 2000 Elsevier Science Ltd.

    DOI: 10.1016/S0040-4039(00)01419-2

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  • A convenient synthesis of trifluoromethyl ethers by oxidative desulfurization-fluorination of dithio carbonates

    K Kanie, Y Tanaka, K Suzuki, M Kuroboshi, T Hiyama

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   73 ( 2 )   471 - 484   2000.2

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    Trifluoromethyl ethers R-OCF3 are easily synthesized from the corresponding dithiocarbonates R-OCS2Me (R = aryl or primary alkyl) by a reagent system consisting of 70% HF/pyridine and an N-halo imide. When the reaction is applied to R-OCS2Me wherein R = secondary alkyl, tertiary alkyl, or benzylic group, fluorination leading to the corresponding alkyl fluorides R-F is achieved, whereas a combination of 50% HF/pyridine and N-bromosuccinimide affords the corresponding trifluoromethyl ethers R-OCF3 (R = secondary).

    DOI: 10.1246/bcsj.73.471

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  • A convenient synthesis of trifluoromethyl ethers by oxidative desulfurization-fluorination of dithiocarbonates

    Kiyoshi Kanie, Yoichiro Tanaka, Kazundo Suzuki, Manabu Kuroboshi, Tamejiro Hiyama

    Bulletin of the Chemical Society of Japan   73 ( 2 )   471 - 484   2000.2

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    Trifluoromethyl ethers R-OCF3 are easily synthesized from the corresponding dithiocarbonates R-OCS2Me (R = aryl or primary alkyl) by a reagent system consisting of 70% HF/pyridine and an N-halo imide. When the reaction is applied to R-OCS2Me wherein R = secondary alkyl, tertiary alkyl, or benzylic group, fluorination leading to the corresponding alkyl fluorides R-F is achieved, whereas a combination of 50% HF/pyridine and N- bromosuccinimide affords the corresponding trifluoromethyl ethers R-OCF3 (R = secondary).

    DOI: 10.1246/bcsj.73.471

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  • A convenient synthesis of trifluoromethyl ethers by oxidative desulfurization-fluorination of dithiocarbonates

    Kiyoshi Kanie, Yoichiro Tanaka, Kazundo Suzuki, Manabu Kuroboshi, Tamejiro Hiyama

    Bulletin of the Chemical Society of Japan   73 ( 2 )   471 - 484   2000.2

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    Trifluoromethyl ethers R-OCF3 are easily synthesized from the corresponding dithiocarbonates R-OCS2Me (R = aryl or primary alkyl) by a reagent system consisting of 70% HF/pyridine and an N-halo imide. When the reaction is applied to R-OCS2Me wherein R = secondary alkyl, tertiary alkyl, or benzylic group, fluorination leading to the corresponding alkyl fluorides R-F is achieved, whereas a combination of 50% HF/pyridine and N- bromosuccinimide affords the corresponding trifluoromethyl ethers R-OCF3 (R = secondary).

    DOI: 10.1246/bcsj.73.471

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  • Tetrakis(dimethylamino)ethylene (TDAE) as a potent organic electron source: Alkenylation of aldehydes using an Ni/Cr/TDAE redox system

    Manabu Kuroboshi, Muneaki Tanaka, Suguru Kishimoto, Kentaro Goto, Misato Mochizuki, Hideo Tanaka

    Tetrahedron Letters   41 ( 1 )   81 - 84   2000.1

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    Tetrakis(dimethylamino)ethylene (TDAE) was found to be a potent organic electron source which could promote alkenylation of several kinds of aldehydes in the presence of a catalytic amount of NiBr2 and CrCl3.

    DOI: 10.1016/S0040-4039(99)02006-7

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  • Tetrakis(dimethylamino)ethylene (TDAE) as a potent organic electron source: Alkenylation of aldehydes using an Ni/Cr/TDAE redox system

    Manabu Kuroboshi, Muneaki Tanaka, Suguru Kishimoto, Kentaro Goto, Misato Mochizuki, Hideo Tanaka

    Tetrahedron Letters   41 ( 1 )   81 - 84   2000.1

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    Tetrakis(dimethylamino)ethylene (TDAE) was found to be a potent organic electron source which could promote alkenylation of several kinds of aldehydes in the presence of a catalytic amount of NiBr2 and CrCl3.

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  • Tetrakis(dimethylamino)ethylene (TDAE) as a potent organic electron source: Alkenylation of aldehydes using an Ni/Cr/TDAE redox system

    Manabu Kuroboshi, Muneaki Tanaka, Suguru Kishimoto, Kentaro Goto, Misato Mochizuki, Hideo Tanaka

    Tetrahedron Letters   41 ( 1 )   81 - 84   2000.1

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    Tetrakis(dimethylamino)ethylene (TDAE) was found to be a potent organic electron source which could promote alkenylation of several kinds of aldehydes in the presence of a catalytic amount of NiBr2 and CrCl3.

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  • Tetrakis(dimethylamino)ethylene (TDAE) as a potent organic electron source: Alkenylation of aldehydes using an Ni/Cr/TDAE redox system

    黒星 学, 田中宗明, 岸本 卓, 後藤健太郎, 望月美里, 田中秀雄

    Tetrahedron Letters   2000

  • 酸化的脱硫フッ素化反応-有機フッ素化合物の簡便合成と新規フッ素系液晶材料の開発-

    黒星 学, 蟹江澄志, 檜山爲次郎

    日本化学会誌 (化学と工業化学)   No. 11pp. 749-761   2000

  • Electro-oxidative kinetic resolution of sec-alcohols by using an optically active N-oxyl mediator

    黒星 学, 吉久裕司, M. N. Cortona, 川上祐介, 高, 欣欽, 田中秀雄

    Tetrahedron Letters   2000

  • Barbier-type allylation of carbonyl derivatives by use of aluminum as an electron pool. Double allylation of carboxylic esters

    H Tanaka, S Nakahata, H Watanabe, JF Zhao, M Kuroboshi, S Torii

    INORGANICA CHIMICA ACTA   296 ( 1 )   204 - 207   1999.12

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    Double allylation of carboxylic esters with allyl bromide was performed successfully by the action of aluminum metal and a catalytic amount of lead(II) bromide in tetrahydrofuran (THF). The proper choice of solvent is essential for the reaction; thus, among the examined solvents, ethers, e.g. THF, 1,2-dimethoxyethane (DME), and diethyl ether, could be successfully used for the double allylation but with N,N-dimethylformamide (DMF), aqueous MeOH, and aqueous THF, no appreciable reaction occurred. Allylation of benzaldehyde dimethyl acetal and N-benzylimine in THF under the same conditions took place smoothly to afford the corresponding allylation products. In a similar manner, allylation of benzonitrile was also performed to afford the doubly allylated benzylamine. (C) 1999 Elsevier Science S.A, All rights reserved.

    DOI: 10.1016/S0020-1693(99)00393-X

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  • Synthesis and electro-optical properties of 3-substituted phenyl trifluoromethyl ethers

    Kiyoshi Kanie, Manabu Kuroboshi, Sadao Takehara, Tamejiro Hiyama

    Journal of Fluorine Chemistry   97 ( 1-2 )   201 - 206   1999.7

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    A convenient synthetic method is described for 3-substituted aromatic trifluoromethyl ethers through an oxidative desulfurization-fluorination reaction. Upon addition to liquid crystalline materials, these ethers lower birefringence (Δn) of the host liquid crystals.

    DOI: 10.1016/S0022-1139(99)00049-4

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  • Synthesis and electro-optical properties of 3-substituted phenyl trifluoromethyl ethers

    Kiyoshi Kanie, Manabu Kuroboshi, Sadao Takehara, Tamejiro Hiyama

    Journal of Fluorine Chemistry   97 ( 1-2 )   201 - 206   1999.7

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    A convenient synthetic method is described for 3-substituted aromatic trifluoromethyl ethers through an oxidative desulfurization-fluorination reaction. Upon addition to liquid crystalline materials, these ethers lower birefringence (Δn) of the host liquid crystals.

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  • Ni/Cr/Al multi-metal redox-mediated alkenylation of aldehydes

    Manabu Kuroboshi, Muneaki Tanaka, Suguru Kishimoto, Kentaro Goto, Hideo Tanaka, Sigeru Torii

    Tetrahedron Letters   40 ( 14 )   2785 - 2788   1999.4

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    Alkenylation of aldehydes mediated by a catalytic amount of Cr(II)/Ni(0), using aluminium as an electron source, was performed to afford the corresponding allyl alcohol derivatives in good to moderate yields.

    DOI: 10.1016/S0040-4039(99)00294-4

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  • Ni/Cr/Al multi-metal redox-mediated alkenylation of aldehydes

    Manabu Kuroboshi, Muneaki Tanaka, Suguru Kishimoto, Kentaro Goto, Hideo Tanaka, Sigeru Torii

    Tetrahedron Letters   40 ( 14 )   2785 - 2788   1999.4

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    Alkenylation of aldehydes mediated by a catalytic amount of Cr(II)/Ni(0), using aluminium as an electron source, was performed to afford the corresponding allyl alcohol derivatives in good to moderate yields.

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  • Ni/Cr/Al multi-metal redox-mediated alkenylation of aldehydes

    Manabu Kuroboshi, Muneaki Tanaka, Suguru Kishimoto, Kentaro Goto, Hideo Tanaka, Sigeru Torii

    Tetrahedron Letters   40 ( 14 )   2785 - 2788   1999.4

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    Alkenylation of aldehydes mediated by a catalytic amount of Cr(II)/Ni(0), using aluminium as an electron source, was performed to afford the corresponding allyl alcohol derivatives in good to moderate yields.

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  • Ni/Cr/Al multi-metal redox-mediated alkenylation of aldehydes

    Manabu Kuroboshi, Muneaki Tanaka, Suguru Kishimoto, Kentaro Goto, Hideo Tanaka, Sigeru Torii

    Tetrahedron Letters   40 ( 14 )   2785 - 2788   1999.4

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    Alkenylation of aldehydes mediated by a catalytic amount of Cr(II)/Ni(0), using aluminium as an electron source, was performed to afford the corresponding allyl alcohol derivatives in good to moderate yields.

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  • Ni/Cr/Al multi-metal redox-mediated alkenylation of aldehydes

    Manabu Kuroboshi, Muneaki Tanaka, Suguru Kishimoto, Kentaro Goto, Hideo Tanaka, Sigeru Torii

    Tetrahedron Letters   40 ( 14 )   2785 - 2788   1999.4

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    Alkenylation of aldehydes mediated by a catalytic amount of Cr(II)/Ni(0), using aluminium as an electron source, was performed to afford the corresponding allyl alcohol derivatives in good to moderate yields.

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  • A facile synthesis of trifluoromethyl- and 3,3,3-trifluoropropenyl-substituted aromatic compounds by the oxidative desulfurization-fluorination of the corresponding carbodithioates

    S Furuta, M Kuroboshi, T Hiyama

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   72 ( 4 )   805 - 819   1999.4

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    Trifluoromethyl-substituted aromatic compounds were easily synthesized by the oxidative desulfurization-fluorination reaction of readily accessible methyl arenecarbodithioates using [n-Bu4N]H2F3 and 1,3-dibromo-5,5-dimethylhydantoin (DBH) under extremely mild conditions. Use of N-bromosuccinimide or N-iodosuccinimide instead of DBH afforded di fluoro(methylthio)methyl-substituted aromatics. In a similar way, 3,3,3-trifluoropropenyl-substituted aromatic compounds were readily prepared from the corresponding alpha,beta-unsaturated carbodithioates.

    DOI: 10.1246/bcsj.72.805

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  • A facile synthesis of trifluoromethyl- and 3,3,3-trifluoropropenyl- substituted aromatic compounds by the oxidative desulfurization-fluorination of the corresponding carbodithioates

    Satoru Furuta, Manabu Kuroboshi, Tamejiro Hiyama

    Bulletin of the Chemical Society of Japan   72 ( 4 )   805 - 819   1999.4

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    Trifluoromethyl-substituted aromatic compounds were easily synthesized by the oxidative desulfurization-fluorination reaction of readily accessible methyl arenecarbodithioates using [n-Bu4N]H2F3 and 1,3-dibromo-5,5- dimethylhydantoin (DBH) under extremely mild conditions. Use of N- bromosuccinimide or N-iodosuccinimide instead of DBH afforded difluoro(methylthio)methyl-substituted aromatics. In a similar way, 3,3,3- trifluoropropenyl-substituted aromatic compounds were readily prepared from the corresponding α,β-unsaturated carbodithioates.

    DOI: 10.1246/bcsj.72.805

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  • Ni/Cr/Al multi-metal redox-mediated alkenylation of aldehydes

    黒星 学, 田中宗明, 岸本 卓, 後藤健太郎, 田中秀雄, 鳥居 滋

    Tetrahedron Letters   1999

  • Synthesis and electro-optical properties of 3-substituted phenyl trifluoromethyl ethers

    蟹江澄志, 黒星 学, 竹原貞夫, 檜山爲次郎

    Journal of Fluorine Chemistry   1999

  • Electrochemical regeneration of chromium(II). Alkenylation of carbonyl compounds

    黒星 学, 田中宗明, 岸本 卓, 田中秀雄, 鳥居 滋

    Synlett   1999

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  • Fluorination of orthothioesters through oxidative desulfurization-fluorination

    古田 理, 黒星 学, 檜山爲次郎

    Bulletin of the Chemical Society of Japan   1999

  • Generation and reaction of copper(I) hydride in the copper(I) chloride-tributyltin hydride-NMP system: Synthesis of 3-norcephalosporin

    田中秀雄, 山口義彦, 角田真一, 黒星 学, 望月美里, 鳥居 滋

    Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio- Organic Chemistry   1999

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  • Syntheses and properties of novel liquid crystals containing a trifluoromethylamino group

    蟹江澄志, 水野克哉, 黒星 学, 竹原貞夫, 檜山爲次郎

    Bulletin of the Chemical Society of Japan   1999

  • Tetrakis(dimethylamino)ethylene (TDAE) as a potent electron source for Cr-mediated allylation of aldehydes and ketones

    黒星 学, 後藤健太郎, 望月美里, 田中秀雄

    Synlett   1999

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  • A facile synthesis of trifluoromethylamines by oxidative desulfurization-fluorination of dithiocarbamates

    K Kanie, K Mizuno, M Kuroboshi, T Hiyama

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   71 ( 8 )   1973 - 1991   1998.8

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    Trifluoromethylamines are easily synthesized from dithiocarbamates by a reagent system consisting of tetrabutylammonium dihydrogentrifluoride and an N-halo imide under mild conditions. When this reaction was applied to dithiocarbamates ArN(R)CS2Me at higher temperatures, the trifluoromethylation was accompanied by halogen substitution at the p-position of the Ar group. The synthesis of trifluoromethyl-substituted adenosine is also described.

    DOI: 10.1246/bcsj.71.1973

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  • Synthesis of 5-substituted 4,4-disubstituted 2-cyclohexen-1-ones by electro-generated base promoted Michael addition of 4,4-disubstituted 2,5-cyclohexadien-1-ones

    S Torii, N Hayashi, M Kuroboshi

    SYNLETT   ( 6 )   599 - +   1998.6

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    5-Substituted 4,4-dialkoxy-2-cyclohexen-1-ones were electrosynthesized from 4,4-disubstituted 2,5-cyclohexadien-1-ones, which were obtained from 1,4-dialkoxybenzene derivatives by electrolysis, by electro-generated base (EG-base)-promoted Michael addition with CH2E2 (E = CO2R, COMe) in moderate to almost quantitative yield. The cyclohexenone derivatives were found to be a good precursor of benzofuranone derivatives through acid-promoted intramolecular lactonization.

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  • Generation and carbonyl addition reactions of dibromofluoromethyllithium derived from tribromofluoromethane as applied to the stereoselective synthesis of fluoro olefins and 2-bromo-2-fluoro-1,3-alkanediols

    Masaki Shimizu, Nobuko Yamada, Yoko Takebe, Takeshi Hata, Manabu Kuroboshi, Tamejiro Hiyama

    Bulletin of the Chemical Society of Japan   71 ( 12 )   2903 - 2921   1998.1

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    The treatment of tribromofluoromethane with BuLi in THF-Et2O (2: 1) at - 130°C generated dibromofluoromethyllithium, which was allowed to react smoothly with a coexisting aldehyde or ketone (RR'C=O) to give fluorinated alcohol RR'C(OH)CFBr2 (3) in good yield. Alcohol 3 was converted stereoselectively to (E)-1-bromo-1,2-difluoro olefin 5 via fluorination with Et2NSF3, followed by dehydrobromination with lithium 2,2,6,6- tetramethylpiperidide, while (E)-1-bromo-1-fluoro olefin was obtained with high selectivity by acetylation of 3, followed by reductive elimination using EtMgBr/(i-Pr)2NH. Difluoro olefin 5 underwent a cross-coupling reaction with an aryl, alkenyl, or alkynylmetal reagent to afford the corresponding fluoro olefin with retention of configuration. On the other hand, the treatment of RCH[OCH2O(CH2)2OCH3]CFBr2 with BuLi at -130°C in the presence of 4- heptanone gave the corresponding adduct diastereoselectively. The stereochemical outcome is explained in terms of chelation between lithium and oxygen atoms of the (2-methoxyethoxy)methyl group. Starting with 2- phenylpropanal, a product is obtained highly selectively containing three contiguous stereocenters including a -CFBr-moiety.

    DOI: 10.1246/bcsj.71.2903

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  • Generation and carbonyl addition reactions of dibromofluoromethyllithium derived from tribromofluoromethane as applied to the stereoselective synthesis of fluoro olefins and 2-bromo-2-fluoro-1,3-alkanediols

    Masaki Shimizu, Nobuko Yamada, Yoko Takebe, Takeshi Hata, Manabu Kuroboshi, Tamejiro Hiyama

    Bulletin of the Chemical Society of Japan   71 ( 12 )   2903 - 2921   1998.1

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    The treatment of tribromofluoromethane with BuLi in THF-Et2O (2: 1) at - 130°C generated dibromofluoromethyllithium, which was allowed to react smoothly with a coexisting aldehyde or ketone (RR'C=O) to give fluorinated alcohol RR'C(OH)CFBr2 (3) in good yield. Alcohol 3 was converted stereoselectively to (E)-1-bromo-1,2-difluoro olefin 5 via fluorination with Et2NSF3, followed by dehydrobromination with lithium 2,2,6,6- tetramethylpiperidide, while (E)-1-bromo-1-fluoro olefin was obtained with high selectivity by acetylation of 3, followed by reductive elimination using EtMgBr/(i-Pr)2NH. Difluoro olefin 5 underwent a cross-coupling reaction with an aryl, alkenyl, or alkynylmetal reagent to afford the corresponding fluoro olefin with retention of configuration. On the other hand, the treatment of RCH[OCH2O(CH2)2OCH3]CFBr2 with BuLi at -130°C in the presence of 4- heptanone gave the corresponding adduct diastereoselectively. The stereochemical outcome is explained in terms of chelation between lithium and oxygen atoms of the (2-methoxyethoxy)methyl group. Starting with 2- phenylpropanal, a product is obtained highly selectively containing three contiguous stereocenters including a -CFBr-moiety.

    DOI: 10.1246/bcsj.71.2903

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  • Generation and carbonyl addition reactions of dibromofluoromethyllithium derived from tribromofluoromethane as applied to the stereoselective synthesis of fluoro olefins and 2-bromo-2-fluoro-1,3-alkanediols

    清水正毅, 山田展子, 武部洋子, 秦 武志, 黒星 学, 檜山爲次郎

    Bulletin of the Chemical Society of Japan   1998

  • Facile synthesis of α-fluoroalkyl sulfides under the oxidative desulfurization-fluorination conditions

    S. Furuta, M. Kuroboshi, T. Hiyama

    Bulletin of the Chemical Society of Japan   71 ( 11 )   2687 - 2694   1998

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    Upon treatment with n-Bu4NH2F3 and 1,3-dibromo-5,5- dimethylhydantoin, various organic sulfides underwent a Pummerer-type rearrangement, followed by fluorination, to give α-fluoro sulfides. The fluoro-Pummerer rearrangement, when applied to RCH(SMe)CF2SMe, gave trifluoro sulfides RCF(SMe)CF2SMe. When an HF-pyridine reagent was used as the fluorinating agent, an oxidative desulfurization-fluorination reaction occurred depending on the structure of the substrates.

    DOI: 10.1246/bcsj.71.2687

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  • Facile synthesis of a-fluoroalkyl sulfides under oxidative desulfurization-fluorination conditions

    古田 理, 黒星 学, 檜山爲次郎

    Bulletin of the Chemical Society of Japan   1998

  • Facile synthesis of α-fluoroalkyl sulfides under the oxidative desulfurization-fluorination conditions

    S. Furuta, M. Kuroboshi, T. Hiyama

    Bulletin of the Chemical Society of Japan   71 ( 11 )   2687 - 2694   1998

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    Upon treatment with n-Bu4NH2F3 and 1,3-dibromo-5,5- dimethylhydantoin, various organic sulfides underwent a Pummerer-type rearrangement, followed by fluorination, to give α-fluoro sulfides. The fluoro-Pummerer rearrangement, when applied to RCH(SMe)CF2SMe, gave trifluoro sulfides RCF(SMe)CF2SMe. When an HF-pyridine reagent was used as the fluorinating agent, an oxidative desulfurization-fluorination reaction occurred depending on the structure of the substrates.

    DOI: 10.1246/bcsj.71.2687

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  • Fluorination of Orthothioesters through Oxidative Desulfurization-Fluorination

    Satoru Furuta, Manabu Kuroboshi, Tamejiro Hiyama

    Bulletin of the Chemical Society of Japan   71 ( 8 )   1939 - 1951   1998

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    The oxidative desulfurization-fluorination of orthothioesters of type RCH2C(SMe)3 using n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin gave bromodifluorination products RCHBrCF2SMe in good yields. The products were converted into bromodifluoro olefins RCBr=CF2 via oxidation and thermolysis. In a similar way, the orthothioesters of type RCH(OH)C(SMe)3 or RCH(OAc)C(SMe)3 were fluorinated to afford difluoro ketones RCOCF2SMe or difluoro acetates RCH(OAc)CF2SMe, respectively. The difiuoro acetates were reduced to RCH(OAc)CF2H by radical reduction. The mechanisms are discussed for difluorination accompanied by bromination or oxidation.

    DOI: 10.1246/bcsj.71.1939

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  • Fluorination of Orthothioesters through Oxidative Desulfurization-Fluorination

    Satoru Furuta, Manabu Kuroboshi, Tamejiro Hiyama

    Bulletin of the Chemical Society of Japan   71 ( 8 )   1939 - 1951   1998

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    The oxidative desulfurization-fluorination of orthothioesters of type RCH2C(SMe)3 using n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin gave bromodifluorination products RCHBrCF2SMe in good yields. The products were converted into bromodifluoro olefins RCBr=CF2 via oxidation and thermolysis. In a similar way, the orthothioesters of type RCH(OH)C(SMe)3 or RCH(OAc)C(SMe)3 were fluorinated to afford difluoro ketones RCOCF2SMe or difluoro acetates RCH(OAc)CF2SMe, respectively. The difiuoro acetates were reduced to RCH(OAc)CF2H by radical reduction. The mechanisms are discussed for difluorination accompanied by bromination or oxidation.

    DOI: 10.1246/bcsj.71.1939

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  • Fluorination of Orthothioesters through Oxidative Desulfurization-Fluorination

    Satoru Furuta, Manabu Kuroboshi, Tamejiro Hiyama

    Bulletin of the Chemical Society of Japan   71 ( 8 )   1939 - 1951   1998

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    The oxidative desulfurization-fluorination of orthothioesters of type RCH2C(SMe)3 using n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin gave bromodifluorination products RCHBrCF2SMe in good yields. The products were converted into bromodifluoro olefins RCBr=CF2 via oxidation and thermolysis. In a similar way, the orthothioesters of type RCH(OH)C(SMe)3 or RCH(OAc)C(SMe)3 were fluorinated to afford difluoro ketones RCOCF2SMe or difluoro acetates RCH(OAc)CF2SMe, respectively. The difiuoro acetates were reduced to RCH(OAc)CF2H by radical reduction. The mechanisms are discussed for difluorination accompanied by bromination or oxidation.

    DOI: 10.1246/bcsj.71.1939

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  • Facile synthesis of α-fluoroalkyl sulfides under the oxidative desulfurization-fluorination conditions

    S. Furuta, M. Kuroboshi, T. Hiyama

    Bulletin of the Chemical Society of Japan   71 ( 11 )   2687 - 2694   1998

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    Upon treatment with n-Bu4NH2F3 and 1,3-dibromo-5,5- dimethylhydantoin, various organic sulfides underwent a Pummerer-type rearrangement, followed by fluorination, to give α-fluoro sulfides. The fluoro-Pummerer rearrangement, when applied to RCH(SMe)CF2SMe, gave trifluoro sulfides RCF(SMe)CF2SMe. When an HF-pyridine reagent was used as the fluorinating agent, an oxidative desulfurization-fluorination reaction occurred depending on the structure of the substrates.

    DOI: 10.1246/bcsj.71.2687

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  • Synthesis of terminal-biradical compounds consisting of two N-oxyl groups connected with conjugated π-systems

    Sigeru Torii, Tomoyuki Hase, Manabu Kuroboshi, Christian Amatore, Anny Jutand, Hiroyuki Kawafuchi

    Tetrahedron Letters   38 ( 42 )   7391 - 7394   1997.10

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    Terminal-biradical compounds 1 having two N-oxyl groups connected with conjugated π-systems were synthesized by (1) addition of magnesium acetylide to 4-oxo-TEMPO, followed by dehydration, or (2) cross-coupling between acetylene and vinyl triflate derived from 4-oxo-TEMPO.

    DOI: 10.1016/S0040-4039(97)01732-2

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  • Synthesis of terminal-biradical compounds consisting of two N-oxyl groups connected with conjugated π-systems

    Sigeru Torii, Tomoyuki Hase, Manabu Kuroboshi, Christian Amatore, Anny Jutand, Hiroyuki Kawafuchi

    Tetrahedron Letters   38 ( 42 )   7391 - 7394   1997.10

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    Terminal-biradical compounds 1 having two N-oxyl groups connected with conjugated π-systems were synthesized by (1) addition of magnesium acetylide to 4-oxo-TEMPO, followed by dehydration, or (2) cross-coupling between acetylene and vinyl triflate derived from 4-oxo-TEMPO.

    DOI: 10.1016/S0040-4039(97)01732-2

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  • Synthesis of terminal-biradical compounds consisting of two N-oxyl groups connected with conjugated π-systems

    Sigeru Torii, Tomoyuki Hase, Manabu Kuroboshi, Christian Amatore, Anny Jutand, Hiroyuki Kawafuchi

    Tetrahedron Letters   38 ( 42 )   7391 - 7394   1997.10

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    Terminal-biradical compounds 1 having two N-oxyl groups connected with conjugated π-systems were synthesized by (1) addition of magnesium acetylide to 4-oxo-TEMPO, followed by dehydration, or (2) cross-coupling between acetylene and vinyl triflate derived from 4-oxo-TEMPO.

    DOI: 10.1016/S0040-4039(97)01732-2

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  • Oxidative desulfurization-fluorination of alkanol xanthates. Control of the reaction pathway to fluorination or trifluoromethoxylation

    Kiyoshi Kanie, Yoichiro Tanaka, Masaki Shimizu, Manabu Kuroboshi, Tamejiro Hiyama

    Chemical Communications   (3), 309-310 ( 3 )   309 - 310   1997

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    The reagent consisting of 70% HF-py (py = pyridine) and a halonium oxidant converts R-OCS2Me into either R-OCF3 (R = primary) or R-F (R = secondary, tertiary or benzylic) whereas the 50% HF-py system converts R-OCS2Me (R = secondary) into R-OCF3.

    DOI: 10.1039/a607897d

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  • Oxidative desulfurization-fluorination of alkanol xanthates. Control of the reaction pathway to fluorination or trifluoromethoxylation

    Kiyoshi Kanie, Yoichiro Tanaka, Masaki Shimizu, Manabu Kuroboshi, Tamejiro Hiyama

    Chemical Communications   (3), 309-310 ( 3 )   309 - 310   1997

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    The reagent consisting of 70% HF-py (py = pyridine) and a halonium oxidant converts R-OCS2Me into either R-OCF3 (R = primary) or R-F (R = secondary, tertiary or benzylic) whereas the 50% HF-py system converts R-OCS2Me (R = secondary) into R-OCF3.

    DOI: 10.1039/a607897d

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  • Diastereoselective generation of lithium carbenoid reagent RCH(OMEM)CFBrLi and its reaction with electrophiles

    Masaki Shimizu, Yoko Takebe, Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   37 ( 41 )   7387 - 7390   1996.10

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    Treatment of RCH(OMEM)CFBr2 with n-BuLi at -130°C in the presence of 4-heptanone gives the corresponding adduct diastereoselectively. The stereochemical outcome is explained in terms of the chelation between lithium and oxygen atoms of the MEM group. Starting with 2-phenylpropanal, a product is produced highly selectively containing three contiguous stereocenters including a -CFBr- moiety.

    DOI: 10.1016/0040-4039(96)01684-X

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  • Diastereoselective generation of lithium carbenoid reagent RCH(OMEM)CFBrLi and its reaction with electrophiles

    Masaki Shimizu, Yoko Takebe, Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   37 ( 41 )   7387 - 7390   1996.10

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    Treatment of RCH(OMEM)CFBr2 with n-BuLi at -130°C in the presence of 4-heptanone gives the corresponding adduct diastereoselectively. The stereochemical outcome is explained in terms of the chelation between lithium and oxygen atoms of the MEM group. Starting with 2-phenylpropanal, a product is produced highly selectively containing three contiguous stereocenters including a -CFBr- moiety.

    DOI: 10.1016/0040-4039(96)01684-X

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  • Catalytic asymmetric hydrosilylation of 1,3-dienes with difluoro(phenyl) silane

    Hideaki Ohmura, Hayao Matsuhashi, Makoto Tanaka, Manabu Kuroboshi, Tamejiro Hiyama, Yasuo Hatanaka, Ken-ichi Goda

    Journal of Organometallic Chemistry   499 ( 1-2 )   167 - 171   1995.9

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    A palladium complex with an optically active ligand catalyzes asymmetric hydrosilylation of 1,3-dienes using difluoro(phenyl)silane to give optically active allyl difluoro(phenyl)silanes in good enantiomeric excess. © 1995.

    DOI: 10.1016/0022-328X(95)00311-D

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  • Catalytic asymmetric hydrosilylation of 1,3-dienes with difluoro(phenyl) silane

    Hideaki Ohmura, Hayao Matsuhashi, Makoto Tanaka, Manabu Kuroboshi, Tamejiro Hiyama, Yasuo Hatanaka, Ken-ichi Goda

    Journal of Organometallic Chemistry   499 ( 1-2 )   167 - 171   1995.9

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    A palladium complex with an optically active ligand catalyzes asymmetric hydrosilylation of 1,3-dienes using difluoro(phenyl)silane to give optically active allyl difluoro(phenyl)silanes in good enantiomeric excess. © 1995.

    DOI: 10.1016/0022-328X(95)00311-D

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  • Catalytic asymmetric hydrosilylation of 1,3-dienes with difluoro(phenyl) silane

    Hideaki Ohmura, Hayao Matsuhashi, Makoto Tanaka, Manabu Kuroboshi, Tamejiro Hiyama, Yasuo Hatanaka, Ken-ichi Goda

    Journal of Organometallic Chemistry   499 ( 1-2 )   167 - 171   1995.9

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    A palladium complex with an optically active ligand catalyzes asymmetric hydrosilylation of 1,3-dienes using difluoro(phenyl)silane to give optically active allyl difluoro(phenyl)silanes in good enantiomeric excess. © 1995.

    DOI: 10.1016/0022-328X(95)00311-D

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  • Catalytic asymmetric hydrosilylation of 1,3-dienes with difluoro(phenyl) silane

    Hideaki Ohmura, Hayao Matsuhashi, Makoto Tanaka, Manabu Kuroboshi, Tamejiro Hiyama, Yasuo Hatanaka, Ken-ichi Goda

    Journal of Organometallic Chemistry   499 ( 1-2 )   167 - 171   1995.9

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    A palladium complex with an optically active ligand catalyzes asymmetric hydrosilylation of 1,3-dienes using difluoro(phenyl)silane to give optically active allyl difluoro(phenyl)silanes in good enantiomeric excess. © 1995.

    DOI: 10.1016/0022-328X(95)00311-D

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  • Catalytic asymmetric hydrosilylation of 1,3-dienes with difluoro(phenyl) silane

    Hideaki Ohmura, Hayao Matsuhashi, Makoto Tanaka, Manabu Kuroboshi, Tamejiro Hiyama, Yasuo Hatanaka, Ken-ichi Goda

    Journal of Organometallic Chemistry   499 ( 1-2 )   167 - 171   1995.9

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    A palladium complex with an optically active ligand catalyzes asymmetric hydrosilylation of 1,3-dienes using difluoro(phenyl)silane to give optically active allyl difluoro(phenyl)silanes in good enantiomeric excess. © 1995.

    DOI: 10.1016/0022-328X(95)00311-D

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  • Stereoselective synthesis of (E)-ArCFCFR and (E)-ArCHCFR from ArCH(OH)CFBr2

    Manabu Kuroboshi, Nobuko Yamada, Yoko Takebe, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 35 )   6271 - 6274   1995.8

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    (E)-vic-Difluoro olefin, RCFCFBr, was synthesized by dehydrobromination of RCFHCFBr2 using lithium 2,2,6,6-tetramethylpiperidide. (E)-Fluoro olefin, RCHCFBr, was obtained by treatment of RCH(OAc)CFBr2 with EtMgBr and HN(i-Pr)2. © 1995.

    DOI: 10.1016/0040-4039(95)01257-I

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  • Stereoselective synthesis of (E)-ArCFCFR and (E)-ArCHCFR from ArCH(OH)CFBr2

    Manabu Kuroboshi, Nobuko Yamada, Yoko Takebe, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 35 )   6271 - 6274   1995.8

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    (E)-vic-Difluoro olefin, RCFCFBr, was synthesized by dehydrobromination of RCFHCFBr2 using lithium 2,2,6,6-tetramethylpiperidide. (E)-Fluoro olefin, RCHCFBr, was obtained by treatment of RCH(OAc)CFBr2 with EtMgBr and HN(i-Pr)2. © 1995.

    DOI: 10.1016/0040-4039(95)01257-I

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  • Stereoselective synthesis of (E)-ArCFCFR and (E)-ArCHCFR from ArCH(OH)CFBr2

    Manabu Kuroboshi, Nobuko Yamada, Yoko Takebe, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 35 )   6271 - 6274   1995.8

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    (E)-vic-Difluoro olefin, RCFCFBr, was synthesized by dehydrobromination of RCFHCFBr2 using lithium 2,2,6,6-tetramethylpiperidide. (E)-Fluoro olefin, RCHCFBr, was obtained by treatment of RCH(OAc)CFBr2 with EtMgBr and HN(i-Pr)2. © 1995.

    DOI: 10.1016/0040-4039(95)01257-I

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  • Stereoselective synthesis of (E)-ArCFCFR and (E)-ArCHCFR from ArCH(OH)CFBr2

    Manabu Kuroboshi, Nobuko Yamada, Yoko Takebe, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 35 )   6271 - 6274   1995.8

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    (E)-vic-Difluoro olefin, RCFCFBr, was synthesized by dehydrobromination of RCFHCFBr2 using lithium 2,2,6,6-tetramethylpiperidide. (E)-Fluoro olefin, RCHCFBr, was obtained by treatment of RCH(OAc)CFBr2 with EtMgBr and HN(i-Pr)2. © 1995.

    DOI: 10.1016/0040-4039(95)01257-I

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  • Oxidative desulfurization-fluorination of 1-substituted 2,2,2-tris(methylthio)ethanol induces difluorination under oxidation or rearrangement

    Manabu Kuroboshi, Satoru Furuta, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 34 )   6121 - 6122   1995.8

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    Oxidative desulfurization-fluorination of RCH(OH)C(SMe)3 using n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin gave RC(O)CF2SMe, whereas treatment of the same substrates with Et2NSF3 afforded RCH(SMe)CF2SMe. © 1995.

    DOI: 10.1016/0040-4039(95)01234-9

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  • Oxidative desulfurization-fluorination of 1-substituted 2,2,2-tris(methylthio)ethanol induces difluorination under oxidation or rearrangement

    Manabu Kuroboshi, Satoru Furuta, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 34 )   6121 - 6122   1995.8

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    Oxidative desulfurization-fluorination of RCH(OH)C(SMe)3 using n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin gave RC(O)CF2SMe, whereas treatment of the same substrates with Et2NSF3 afforded RCH(SMe)CF2SMe. © 1995.

    DOI: 10.1016/0040-4039(95)01234-9

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  • Oxidative desulfurization-fluorination of 1-substituted 2,2,2-tris(methylthio)ethanol induces difluorination under oxidation or rearrangement

    Manabu Kuroboshi, Satoru Furuta, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 34 )   6121 - 6122   1995.8

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    Oxidative desulfurization-fluorination of RCH(OH)C(SMe)3 using n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin gave RC(O)CF2SMe, whereas treatment of the same substrates with Et2NSF3 afforded RCH(SMe)CF2SMe. © 1995.

    DOI: 10.1016/0040-4039(95)01234-9

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  • Palladium-catalyzed cross-coupling of allylic carbonates with alkenylfluorosilanes in the absence of fluoride ion

    Hayao Matsuhashi, Yasuo Hatanaka, Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 9 )   1539 - 1540   1995.2

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    Alkenylfluorosilanes smoothly underwent cross-coupling reaction with allylic carbonates in the presence of a palladium catalyst andin the absence of fluoride ion to give 1, 4-dienes in good yields with retention of configuration. © 1995 Elsevier Science Ltd.

    DOI: 10.1016/0040-4039(95)00082-N

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  • Palladium-catalyzed cross-coupling of allylic carbonates with alkenylfluorosilanes in the absence of fluoride ion

    Hayao Matsuhashi, Yasuo Hatanaka, Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 9 )   1539 - 1540   1995.2

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    Alkenylfluorosilanes smoothly underwent cross-coupling reaction with allylic carbonates in the presence of a palladium catalyst andin the absence of fluoride ion to give 1, 4-dienes in good yields with retention of configuration. © 1995 Elsevier Science Ltd.

    DOI: 10.1016/0040-4039(95)00082-N

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  • Palladium-catalyzed cross-coupling of allylic carbonates with alkenylfluorosilanes in the absence of fluoride ion

    Hayao Matsuhashi, Yasuo Hatanaka, Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 9 )   1539 - 1540   1995.2

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    Alkenylfluorosilanes smoothly underwent cross-coupling reaction with allylic carbonates in the presence of a palladium catalyst andin the absence of fluoride ion to give 1, 4-dienes in good yields with retention of configuration. © 1995 Elsevier Science Ltd.

    DOI: 10.1016/0040-4039(95)00082-N

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  • Palladium-catalyzed cross-coupling of allylic carbonates with alkenylfluorosilanes in the absence of fluoride ion

    Hayao Matsuhashi, Yasuo Hatanaka, Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 9 )   1539 - 1540   1995.2

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    Alkenylfluorosilanes smoothly underwent cross-coupling reaction with allylic carbonates in the presence of a palladium catalyst andin the absence of fluoride ion to give 1, 4-dienes in good yields with retention of configuration. © 1995 Elsevier Science Ltd.

    DOI: 10.1016/0040-4039(95)00082-N

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  • Synthesis of trifluoromethylamino-substituted pyridines and pyrimidines by oxidative desulfurization-fluorination

    Manabu Kuroboshi, Katsuya Mizuno, Kiyoshi Kanie, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 4 )   563 - 566   1995.1

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    Oxidative desulfurization-fluorination of methyl N-pyridyl(or N-pyrimidyl)-N-alkyldithiocarbamates gave the corresponding trifluoromethylamino-substituted pyridines (or pyrimidines), which underwent cross-coupling reaction to give a new type of liquid crystalline compounds having trifluoromethylamino group. © 1995.

    DOI: 10.1016/0040-4039(94)02253-8

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  • Fluoro-Pummerer rearrangement under oxidative desulfurization fluorination conditions. Facile synthesis of oligofluoroalkyl sulfides

    Satoru Furuta, Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 45 )   8243 - 8246   1995

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    Upon treatment with n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin, various organic sulfides were readily fluorinated to give α-fluoro sulfides. When (HF)9-Py was used as the fluorinating agent, normal oxidative desulfurization fluorination occurred depending on the structure of the substrates.

    DOI: 10.1016/0040-4039(95)01768-D

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  • Fluoro-Pummerer rearrangement under oxidative desulfurization fluorination conditions. Facile synthesis of oligofluoroalkyl sulfides

    Satoru Furuta, Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 45 )   8243 - 8246   1995

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    Upon treatment with n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin, various organic sulfides were readily fluorinated to give α-fluoro sulfides. When (HF)9-Py was used as the fluorinating agent, normal oxidative desulfurization fluorination occurred depending on the structure of the substrates.

    DOI: 10.1016/0040-4039(95)01768-D

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  • Fluoro-Pummerer rearrangement under oxidative desulfurization fluorination conditions. Facile synthesis of oligofluoroalkyl sulfides

    Satoru Furuta, Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   36 ( 45 )   8243 - 8246   1995

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    Upon treatment with n-Bu4NH2F3 and 1,3-dibromo-5,5-dimethylhydantoin, various organic sulfides were readily fluorinated to give α-fluoro sulfides. When (HF)9-Py was used as the fluorinating agent, normal oxidative desulfurization fluorination occurred depending on the structure of the substrates.

    DOI: 10.1016/0040-4039(95)01768-D

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  • Palladium catalyzed cross-coupling reaction of functionalized alkyltrifluorosilanes with aryl halides

    Hayao Matsuhashi, Manabu Kuroboshi, Yasuo Hatanaka, Tamejiro Hiyama

    Tetrahedron Letters   35 ( 35 )   6507 - 6510   1994.8

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    A variety of alkyltrifluorosilanes were found to couple with aryl halides in the presence of Pd(PPh3)4 catalyst and tetrabutylammonium fluoride (TBAF) to give the corresponding cross-coupled products in moderate to good yields. © 1994.

    DOI: 10.1016/S0040-4039(00)78258-X

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  • Palladium catalyzed cross-coupling reaction of functionalized alkyltrifluorosilanes with aryl halides

    Hayao Matsuhashi, Manabu Kuroboshi, Yasuo Hatanaka, Tamejiro Hiyama

    Tetrahedron Letters   35 ( 35 )   6507 - 6510   1994.8

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    A variety of alkyltrifluorosilanes were found to couple with aryl halides in the presence of Pd(PPh3)4 catalyst and tetrabutylammonium fluoride (TBAF) to give the corresponding cross-coupled products in moderate to good yields. © 1994.

    DOI: 10.1016/S0040-4039(00)78258-X

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  • Asymmetric reduction of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones with lithium aluminum hydride or diisobutylaluminum hydride. Highly stereoselective synthesis of 2-fluoro-2-(trifluoromethyl)-1,3-diols

    Takashi Ishihara, Koichi Yamaguchi, Manabu Kuroboshi, Kiitiro Utimoto

    Tetrahedron Letters   35 ( 29 )   5263 - 5266   1994.7

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    The syn and anti isomers of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones are reduced in a highly 1,2-syn diastereoselective manner with lithium aluminum hydride or diisobutylaluminum hydride in tetrahydrofuran at -78 °C, affording 1,2-syn-2,3-syn- and 1,2-syn-2,3-anti-2-fluoro-2-(trifluoromethyl)-1,3-diols, respectively, in excellent yields. High 1,2-syn stereoselectivity in the reduction can be ascribed to the presence of the 2-trifluoromethyl substituent. © 1994.

    DOI: 10.1016/S0040-4039(00)77080-8

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  • Asymmetric reduction of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones with lithium aluminum hydride or diisobutylaluminum hydride. Highly stereoselective synthesis of 2-fluoro-2-(trifluoromethyl)-1,3-diols

    Takashi Ishihara, Koichi Yamaguchi, Manabu Kuroboshi, Kiitiro Utimoto

    Tetrahedron Letters   35 ( 29 )   5263 - 5266   1994.7

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    The syn and anti isomers of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones are reduced in a highly 1,2-syn diastereoselective manner with lithium aluminum hydride or diisobutylaluminum hydride in tetrahydrofuran at -78 °C, affording 1,2-syn-2,3-syn- and 1,2-syn-2,3-anti-2-fluoro-2-(trifluoromethyl)-1,3-diols, respectively, in excellent yields. High 1,2-syn stereoselectivity in the reduction can be ascribed to the presence of the 2-trifluoromethyl substituent. © 1994.

    DOI: 10.1016/S0040-4039(00)77080-8

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  • Asymmetric reduction of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones with lithium aluminum hydride or diisobutylaluminum hydride. Highly stereoselective synthesis of 2-fluoro-2-(trifluoromethyl)-1,3-diols

    Takashi Ishihara, Koichi Yamaguchi, Manabu Kuroboshi, Kiitiro Utimoto

    Tetrahedron Letters   35 ( 29 )   5263 - 5266   1994.7

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    The syn and anti isomers of 2-fluoro-2-(trifluoromethyl)-3-hydroxy ketones are reduced in a highly 1,2-syn diastereoselective manner with lithium aluminum hydride or diisobutylaluminum hydride in tetrahydrofuran at -78 °C, affording 1,2-syn-2,3-syn- and 1,2-syn-2,3-anti-2-fluoro-2-(trifluoromethyl)-1,3-diols, respectively, in excellent yields. High 1,2-syn stereoselectivity in the reduction can be ascribed to the presence of the 2-trifluoromethyl substituent. © 1994.

    DOI: 10.1016/S0040-4039(00)77080-8

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  • A convenient synthesis of perfluoroalkylated amines by oxidative desulfurization-fluorination

    Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   35 ( 23 )   3983 - 3984   1994.6

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    N-Perfluoroalkylamines were synthesized from perfluoroalkanethioamides, which were easily accessible from perfluoroalkanamides, by the action of N-halo imide and nBu4NH2F3. © 1994.

    DOI: 10.1016/S0040-4039(00)76719-0

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  • A convenient synthesis of perfluoroalkylated amines by oxidative desulfurization-fluorination

    Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   35 ( 23 )   3983 - 3984   1994.6

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    N-Perfluoroalkylamines were synthesized from perfluoroalkanethioamides, which were easily accessible from perfluoroalkanamides, by the action of N-halo imide and nBu4NH2F3. © 1994.

    DOI: 10.1016/S0040-4039(00)76719-0

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  • Synthesis of perfluoroalkyl-substituted arenes by oxidative desulfurization-fluorination

    Manabu Kuroboshi, Tamejiro Hiyama

    Journal of Fluorine Chemistry   69 ( 2 )   127 - 128   1994

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    Perfluoroalkyl-substituted arenes have been readily synthesized from 2-aryl-2-perfluoroalkyl-1,3-dithiolanes by the action of an N-halo imide and HF/pyridine (or HF/melamine). © 1994.

    DOI: 10.1016/0022-1139(94)03139-8

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  • Oxidative desulfurization-fluorination of xanthates. A convenient synthesis of trifluoromethyl ethers and difluoro(methylthio)methyl ethers

    Manabu Kuroboshi, Kazundo Suzuki, Tamejiro Hiyama

    Tetrahedron Letters   33 ( 29 )   4173 - 4176   1992.7

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    Treatment of xanthates R-OC(S)SMe with (HF)9/Py and 1,3-dibromo-5,5-dimethylhydantoin gives trifluoromethyl ethers R-OCF3 through intermediates R-OCF2SMe, which could be isolated upon treatment of xanthates with n-Bu4N+H2F3- and N-bromosuccinimide. © 1992.

    DOI: 10.1016/S0040-4039(00)74681-8

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  • A facile synthesis of trifluoromethylamines by oxidative desulfurization-fluorination of dithiocarbamates

    Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   33 ( 29 )   4177 - 4178   1992.7

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    Reaction of methyl dithiocarbamates R1R2N-C(S)SMe with n-Bu4N+H2F3- and N-bromosuccinimide provides trifluoromethylamines R1R2N-CF3 in good yields. © 1992.

    DOI: 10.1016/S0040-4039(00)74682-X

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  • A facile synthesis of trifluoromethylamines by oxidative desulfurization-fluorination of dithiocarbamates

    Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   33 ( 29 )   4177 - 4178   1992.7

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    Reaction of methyl dithiocarbamates R1R2N-C(S)SMe with n-Bu4N+H2F3- and N-bromosuccinimide provides trifluoromethylamines R1R2N-CF3 in good yields. © 1992.

    DOI: 10.1016/S0040-4039(00)74682-X

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  • Oxidative desulfurization-fluorination of xanthates. A convenient synthesis of trifluoromethyl ethers and difluoro(methylthio)methyl ethers

    Manabu Kuroboshi, Kazundo Suzuki, Tamejiro Hiyama

    Tetrahedron Letters   33 ( 29 )   4173 - 4176   1992.7

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    Treatment of xanthates R-OC(S)SMe with (HF)9/Py and 1,3-dibromo-5,5-dimethylhydantoin gives trifluoromethyl ethers R-OCF3 through intermediates R-OCF2SMe, which could be isolated upon treatment of xanthates with n-Bu4N+H2F3- and N-bromosuccinimide. © 1992.

    DOI: 10.1016/S0040-4039(00)74681-8

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  • Oxidative desulfurization-fluorination of xanthates. A convenient synthesis of trifluoromethyl ethers and difluoro(methylthio)methyl ethers

    Manabu Kuroboshi, Kazundo Suzuki, Tamejiro Hiyama

    Tetrahedron Letters   33 ( 29 )   4173 - 4176   1992.7

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    Treatment of xanthates R-OC(S)SMe with (HF)9/Py and 1,3-dibromo-5,5-dimethylhydantoin gives trifluoromethyl ethers R-OCF3 through intermediates R-OCF2SMe, which could be isolated upon treatment of xanthates with n-Bu4N+H2F3- and N-bromosuccinimide. © 1992.

    DOI: 10.1016/S0040-4039(00)74681-8

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  • Halofluorination of alkenes using tetrabutylammonium dihydrogentrifluoride

    Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   32 ( 9 )   1215 - 1218   1991.2

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    Regio-, stereo-, and chemoselective halofluorination of alkenes is achieved using N-haloamides and tetrabutylammonium dihydrogentrifluoride, and the resulting F-I adducts were successfully converted into fluoroalkenes under dehydroiodination with 1,8-diazabicyclo[5.4.0]undec-7-ene. © 1991.

    DOI: 10.1016/S0040-4039(00)92048-3

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  • Halofluorination of alkenes using tetrabutylammonium dihydrogentrifluoride

    Manabu Kuroboshi, Tamejiro Hiyama

    Tetrahedron Letters   32 ( 9 )   1215 - 1218   1991.2

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    Regio-, stereo-, and chemoselective halofluorination of alkenes is achieved using N-haloamides and tetrabutylammonium dihydrogentrifluoride, and the resulting F-I adducts were successfully converted into fluoroalkenes under dehydroiodination with 1,8-diazabicyclo[5.4.0]undec-7-ene. © 1991.

    DOI: 10.1016/S0040-4039(00)92048-3

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  • ZINC-COPPER(I) CHLORIDE OR ZINC-SILVER ACETATE PROMOTED COUPLING REACTION OF 2-[(TRIMETHYLSILYL)METHYL]-3-CHLORO-3,3-DIFLUOROPROPENE WITH CARBONYL-COMPOUNDS - HIGHLY EFFICIENT ACCESS TO 2,2-DIFLUORO HOMOALLYL ALCOHOLS

    T ISHIHARA, S MIWATASHI, M KUROBOSHI, K UTIMOTO

    TETRAHEDRON LETTERS   32 ( 8 )   1069 - 1072   1991.2

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    2-[(Trimethylsilyl]methyl]-3-chloro-3,3-difluoropropene, readily prepared in two steps from methyl chlorodifluoroacetate and (trimethylsilyl)methylmagnesium chloride, is reduced to couple regioselectively with a variety of carbonly compounds in the presence of zinc-copper(l) chloride or -silver acetate to give 2,2-difluoro-3-[(trimethylsilyl)methyl]-3-buten-1-ol derivatives in good to excellent yields.

    DOI: 10.1016/S0040-4039(00)74490-X

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  • ZINC-COPPER(I) CHLORIDE OR ZINC-SILVER ACETATE PROMOTED COUPLING REACTION OF 2-[(TRIMETHYLSILYL)METHYL]-3-CHLORO-3,3-DIFLUOROPROPENE WITH CARBONYL-COMPOUNDS - HIGHLY EFFICIENT ACCESS TO 2,2-DIFLUORO HOMOALLYL ALCOHOLS

    T ISHIHARA, S MIWATASHI, M KUROBOSHI, K UTIMOTO

    TETRAHEDRON LETTERS   32 ( 8 )   1069 - 1072   1991.2

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    2-[(Trimethylsilyl]methyl]-3-chloro-3,3-difluoropropene, readily prepared in two steps from methyl chlorodifluoroacetate and (trimethylsilyl)methylmagnesium chloride, is reduced to couple regioselectively with a variety of carbonly compounds in the presence of zinc-copper(l) chloride or -silver acetate to give 2,2-difluoro-3-[(trimethylsilyl)methyl]-3-buten-1-ol derivatives in good to excellent yields.

    DOI: 10.1016/S0040-4039(00)74490-X

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  • An Efficient Generation of The Aluminum Enolates of 1H-Perfluoroalkyl Ketones From 1-Substituted-1-Perfluoroalkenyl Phosphates and Their Aldol Reaction with Aldehydes1

    Takashi Ishihara Manabu Kuroboshi, Manabu Kuroboshi, Koichi Yamaguchi, Yoshiji Okada

    Journal of Organic Chemistry   55 ( 10 )   3107 - 3114   1990

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    Diethyl 1-substituted-1-perfluoroalkenyl phosphates (1), available from perfluoroalkyl ketones and sodium diethyl phosphite, were allowed to react with a reagent derived from lithium aluminum hydride and a metal salt or brominein tetrahydrofuran below -30 °C and successively treated with water or aldehydes to give rise to the corresponding 1H-perfluoroalkyl ketones (4) or a-fluoro-a-perfluoroalkyl-β-hydroxy ketones (5), respectively, in moderate to good yields. Copper(II) bromide, copper(I) bromide, and zinc chloride could be employed as the metal salt in the reaction. The phosphates also underwent reductive dephosphorylation with diisobutylaluminum hydride to generate the aluminum enolates of 1H-perfluoroalkyl ketones. 19F NMR analyses indicated that their structure is not an α-metallo ketone but an oxygen-metalated species and that they are appreciably stable below 0 °C. Treatment with a wide variety of aldehydes at 0 °C yielded the corresponding aldol products 5 in good to excellent yields, whereas ketones did not react. © 1990, American Chemical Society. All rights reserved.

    DOI: 10.1021/jo00297a028

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  • An Efficient Generation of The Aluminum Enolates of 1H-Perfluoroalkyl Ketones From 1-Substituted-1-Perfluoroalkenyl Phosphates and Their Aldol Reaction with Aldehydes1

    Takashi Ishihara Manabu Kuroboshi, Manabu Kuroboshi, Koichi Yamaguchi, Yoshiji Okada

    Journal of Organic Chemistry   55 ( 10 )   3107 - 3114   1990

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    Diethyl 1-substituted-1-perfluoroalkenyl phosphates (1), available from perfluoroalkyl ketones and sodium diethyl phosphite, were allowed to react with a reagent derived from lithium aluminum hydride and a metal salt or brominein tetrahydrofuran below -30 °C and successively treated with water or aldehydes to give rise to the corresponding 1H-perfluoroalkyl ketones (4) or a-fluoro-a-perfluoroalkyl-β-hydroxy ketones (5), respectively, in moderate to good yields. Copper(II) bromide, copper(I) bromide, and zinc chloride could be employed as the metal salt in the reaction. The phosphates also underwent reductive dephosphorylation with diisobutylaluminum hydride to generate the aluminum enolates of 1H-perfluoroalkyl ketones. 19F NMR analyses indicated that their structure is not an α-metallo ketone but an oxygen-metalated species and that they are appreciably stable below 0 °C. Treatment with a wide variety of aldehydes at 0 °C yielded the corresponding aldol products 5 in good to excellent yields, whereas ketones did not react. © 1990, American Chemical Society. All rights reserved.

    DOI: 10.1021/jo00297a028

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  • An Efficient Generation of The Aluminum Enolates of 1H-Perfluoroalkyl Ketones From 1-Substituted-1-Perfluoroalkenyl Phosphates and Their Aldol Reaction with Aldehydes1

    Takashi Ishihara Manabu Kuroboshi, Manabu Kuroboshi, Koichi Yamaguchi, Yoshiji Okada

    Journal of Organic Chemistry   55 ( 10 )   3107 - 3114   1990

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    Diethyl 1-substituted-1-perfluoroalkenyl phosphates (1), available from perfluoroalkyl ketones and sodium diethyl phosphite, were allowed to react with a reagent derived from lithium aluminum hydride and a metal salt or brominein tetrahydrofuran below -30 °C and successively treated with water or aldehydes to give rise to the corresponding 1H-perfluoroalkyl ketones (4) or a-fluoro-a-perfluoroalkyl-β-hydroxy ketones (5), respectively, in moderate to good yields. Copper(II) bromide, copper(I) bromide, and zinc chloride could be employed as the metal salt in the reaction. The phosphates also underwent reductive dephosphorylation with diisobutylaluminum hydride to generate the aluminum enolates of 1H-perfluoroalkyl ketones. 19F NMR analyses indicated that their structure is not an α-metallo ketone but an oxygen-metalated species and that they are appreciably stable below 0 °C. Treatment with a wide variety of aldehydes at 0 °C yielded the corresponding aldol products 5 in good to excellent yields, whereas ketones did not react. © 1990, American Chemical Society. All rights reserved.

    DOI: 10.1021/jo00297a028

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  • An efficient and general method for the reformatsky-type reaction of chlorodifluoromethyl ketones with carbonyl compounds giving α,α-difluoro-β-hydroxy ketones1)

    M. Kuroboshi, T. Ishihara

    Bulletin of the Chemical Society of Japan   63 ( 2 )   428 - 437   1990

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    Chlorodifluoromethyl ketones CF2ClCOR, where R is an alkyl, aryl, and l-alkynyl group, underwent the Reformatsky-type aldol reaction with a wide variety of aldehydes or ketones in the presence of acid-washed zinc dust and copper(I) chloride or silver acetate to give the corresponding α,α-difluoro-β-hydroxy ketones in good to excellent yields. Specific activation of zinc metal with the metal salt is essential to achieve high efficiency of the reaction, depending upon the structures of the chlorodifluoromethyl ketones and the carbonyl compounds employed. In-situ formed intermediates in these reactions were successfully detected by 19F NMR spectroscopy, which suggests that their structure is not an α-metallo ketone but an oxygen-metallated species possessing the zinc(II) metal as counter cation.

    DOI: 10.1246/bcsj.63.428

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  • Addition reactions of F-alkyl iodides to carbon-carbon double bonds promoted by metallic tin(0)-metal salt systems

    Manabu Kuroboshi, Takashi Ishihara

    Journal of Fluorine Chemistry   39 ( 2 )   299 - 303   1988

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    F-alkyl iodides readily reacted with a variety of alkenes in methanol at room temperature under the influence of metallic tin(0)-silver(I) acetate of metallic tin(0)-copper(I) chloride to afford the corresponding addition products, F- alkylated iodides, in good to excellent yields. This addition reaction was also promoted by the use of a metallic tin(0)- aluminium(0) reagent, though gentle heating was necessary for allowing the reaction to proceed. © 1988.

    DOI: 10.1016/S0022-1139(00)82786-4

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  • Facile transformation of 1-substituted F-1-alkenyl phosphates into polyfluorinated 1,3-dienes by use of phosphonium ylides

    Yoshiji Okada, Manabu Kuroboshi, Takashi Ishihara

    Journal of Fluorine Chemistry   41 ( 3 )   435 - 438   1988

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    1-Substituted F-1-alkenyl phosphates, easily prepared from F-alkyl ketones and the sodium salt of diethyl phosphite, were allowed to react with various phosphonium ylides in tetrahydrofuran or hexane at room temperature or at the reflux temperature of the solvent to lead to the corresponding polyfluorinated 1,3-diene derivatives in moderate to good yields. © 1988.

    DOI: 10.1016/S0022-1139(00)81045-3

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  • Facile transformation of 1-substituted F-1-alkenyl phosphates into polyfluorinated 1,3-dienes by use of phosphonium ylides

    Yoshiji Okada, Manabu Kuroboshi, Takashi Ishihara

    Journal of Fluorine Chemistry   41 ( 3 )   435 - 438   1988

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    1-Substituted F-1-alkenyl phosphates, easily prepared from F-alkyl ketones and the sodium salt of diethyl phosphite, were allowed to react with various phosphonium ylides in tetrahydrofuran or hexane at room temperature or at the reflux temperature of the solvent to lead to the corresponding polyfluorinated 1,3-diene derivatives in moderate to good yields. © 1988.

    DOI: 10.1016/S0022-1139(00)81045-3

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  • Selective preparation of 1-substituted 2,2-difluoroethenyl phosphates or 1-hydroxyalkanephosphonates through the reaction of chlorodifluoromethyl ketones with dialkyl or diaryl phosphites

    Takashi Ishihara, Masayuki Yamana, Takashige Maekawa, Manabu Kuroboshi, Teiichi Ando

    Journal of Fluorine Chemistry   38 ( 2 )   263 - 277   1988

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    Various chlorodifluoromethyl ketones react readily with dialkyl or diaryl phosphites in the presence of triethylamine at the reflux temperature of tetrahydrofuran to give the corresponding dialkyl or diaryl 1-substituted-2,2-difluoroethenyl phosphates in good yields, whereas the similar reaction conducted at lower temperature (0-20 °C) affords 1-(chlorodifluoromethyl)-1-hydroxyalkanephosphonates almost exclusively. The latter compounds are converted to the former enol phosphates by the treatment with triethylamine or sodium methoxide in refluxing tetrahydrofuran. © 1988.

    DOI: 10.1016/S0022-1139(00)83035-3

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  • Selective preparation of 1-substituted 2,2-difluoroethenyl phosphates or 1-hydroxyalkanephosphonates through the reaction of chlorodifluoromethyl ketones with dialkyl or diaryl phosphites

    Takashi Ishihara, Masayuki Yamana, Takashige Maekawa, Manabu Kuroboshi, Teiichi Ando

    Journal of Fluorine Chemistry   38 ( 2 )   263 - 277   1988

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    Various chlorodifluoromethyl ketones react readily with dialkyl or diaryl phosphites in the presence of triethylamine at the reflux temperature of tetrahydrofuran to give the corresponding dialkyl or diaryl 1-substituted-2,2-difluoroethenyl phosphates in good yields, whereas the similar reaction conducted at lower temperature (0-20 °C) affords 1-(chlorodifluoromethyl)-1-hydroxyalkanephosphonates almost exclusively. The latter compounds are converted to the former enol phosphates by the treatment with triethylamine or sodium methoxide in refluxing tetrahydrofuran. © 1988.

    DOI: 10.1016/S0022-1139(00)83035-3

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  • Selective preparation of 1-substituted 2,2-difluoroethenyl phosphates or 1-hydroxyalkanephosphonates through the reaction of chlorodifluoromethyl ketones with dialkyl or diaryl phosphites

    Takashi Ishihara, Masayuki Yamana, Takashige Maekawa, Manabu Kuroboshi, Teiichi Ando

    Journal of Fluorine Chemistry   38 ( 2 )   263 - 277   1988

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    Various chlorodifluoromethyl ketones react readily with dialkyl or diaryl phosphites in the presence of triethylamine at the reflux temperature of tetrahydrofuran to give the corresponding dialkyl or diaryl 1-substituted-2,2-difluoroethenyl phosphates in good yields, whereas the similar reaction conducted at lower temperature (0-20 °C) affords 1-(chlorodifluoromethyl)-1-hydroxyalkanephosphonates almost exclusively. The latter compounds are converted to the former enol phosphates by the treatment with triethylamine or sodium methoxide in refluxing tetrahydrofuran. © 1988.

    DOI: 10.1016/S0022-1139(00)83035-3

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  • Zinc-copper(I) chloride or -silver(I) acetate promoted aldol reaction of chlorodifluoromethyl ketones with carbonyl compounds. A general and effective route to α,α-difuluoro-β-hydroxy ketones

    Manabu Kuroboshi, Takashi Ishihara

    Tetrahedron Letters   28 ( 51 )   6481 - 6484   1987

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    Chlorodifluoromethyl ketones efficiently underwent the aldol reaction with a variety of aldehydes or ketones in the presence of zinc, a catalytic amount of copper(I) chloride or silver(I) acetate and molecular sieves to give the corresponding α,α-difluoro-β-hydroxy ketones in good to excellent yields. © 1987.

    DOI: 10.1016/S0040-4039(00)96894-1

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  • A CONVENIENT SYNTHESIS OF FLUORINE-CONTAINING HIGHLY-SUBSTITUTED FURANS THROUGH NEW FLUORIDE ION-CATALYZED REACTION OF 1-ALKYL-F-1-ALKENYL PHOSPHATES

    M KUROBOSHI, T SHINOZAKI, T ISHIHARA, T ANDO

    CHEMISTRY LETTERS   (8), 1621-1622 ( 8 )   1621 - 1622   1987

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    Language:English   Publisher:CHEMICAL SOC JAPAN  

    DOI: 10.1246/cl.1987.1621

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  • A CONVENIENT SYNTHESIS OF FLUORINE-CONTAINING HIGHLY-SUBSTITUTED FURANS THROUGH NEW FLUORIDE ION-CATALYZED REACTION OF 1-ALKYL-F-1-ALKENYL PHOSPHATES

    M KUROBOSHI, T SHINOZAKI, T ISHIHARA, T ANDO

    CHEMISTRY LETTERS   (8), 1621-1622 ( 8 )   1621 - 1622   1987

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    Language:English   Publisher:CHEMICAL SOC JAPAN  

    DOI: 10.1246/cl.1987.1621

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  • Highly effective dephosphorylation of F-1-alkenyl phosphates with copper halide-lithium aluminium hydride reagent: A new access to 1-hydryl-F-alkyl ketones from F-alkyl ketones

    Takashi Ishihara, Manabu Kuroboshi

    Journal of Fluorine Chemistry   37 ( 1 )   113 - 118   1987

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    1-Substituted F-1-alkenyl phosphate, readily available from F-alkyl ketones and diethyl phosphite, undergo the dephosphorylation by the action of copper(I) or copper(II) bromide and lithium aluminium hydride at -78 °C followed by hydrolysis to give the corresponding 1-hydryl-F-alkyl ketones in good to excellent yields. © 1987.

    DOI: 10.1016/S0022-1139(00)83092-4

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  • Highly effective dephosphorylation of F-1-alkenyl phosphates with copper halide-lithium aluminium hydride reagent: A new access to 1-hydryl-F-alkyl ketones from F-alkyl ketones

    Takashi Ishihara, Manabu Kuroboshi

    Journal of Fluorine Chemistry   37 ( 1 )   113 - 118   1987

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    1-Substituted F-1-alkenyl phosphate, readily available from F-alkyl ketones and diethyl phosphite, undergo the dephosphorylation by the action of copper(I) or copper(II) bromide and lithium aluminium hydride at -78 °C followed by hydrolysis to give the corresponding 1-hydryl-F-alkyl ketones in good to excellent yields. © 1987.

    DOI: 10.1016/S0022-1139(00)83092-4

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  • A CONVENIENT SYNTHESIS OF FLUORINE-CONTAINING HIGHLY-SUBSTITUTED FURANS THROUGH NEW FLUORIDE ION-CATALYZED REACTION OF 1-ALKYL-F-1-ALKENYL PHOSPHATES

    M KUROBOSHI, T SHINOZAKI, T ISHIHARA, T ANDO

    CHEMISTRY LETTERS   (8), 1621-1622 ( 8 )   1621 - 1622   1987

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    Language:English   Publisher:CHEMICAL SOC JAPAN  

    DOI: 10.1246/cl.1987.1621

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Presentations

  • #618 Electrooxidative Desulfurization/Chlorination. A Facile Synthesis of 4-Chloro-2-azetidinones, A Potent Intermediate for Carbapenems

    215th ECS Meeting  2009 

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  • #623 Electroreductive Intramolecular Cyclization of Aryl Halides Using Fluorene Mediators

    215th ECS Meeting  2009 

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  • 電解塩素化を活用する 4-クロロ-2-アゼチジノンの合成

    日本化学会第89春季年会  2009 

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  • ビオロゲンの電解還元による有機還元剤の発生と反応。アリール/アリールカップリングへの展開

    日本化学会第89春季年会  2009 

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  • 活性炭に吸着した芳香族ハロゲン化物の電解還元脱ハロゲン化

    日本化学会第89春季年会  2009 

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  • Al/MXn複合レドックス系を用いるトリフェニルホスフィンオキシドからトリフェニルホスフィンへの One-pot 変換

    日本化学会第89春季年会  2009 

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  • 水中での電解還元による有機還元剤の調製と炭素-炭素結合形成への応用

    2009年電気化学秋季大会  2009 

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  • Ph3P のリサイクルシステムを指向した五価リン化合物の還元反応

    第33回有機電子移動化学討論会  2009 

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  • 電解還元を利用する再利用可能な有機還元剤の調製とその利用

    第33回有機電子移動化学討論会  2009 

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  • #1673 Ni-Catalyzed Electroreductive Dehalogenation of Aryl Halides

    216th ECS Meeting  2009 

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  • 電解塩素化を鍵プロセスとする 4-クロロアゼチジノンの合成

    2009年電気化学秋季大会  2009 

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  • #535 Pd/Viologen-Promoted Reductive Coupling of Aryl Halides in

    213th ECS Meeting  2008 

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  • #562 Electroreductive Dehalogenation/Dimerization of Aryl Halides on an Activated Carbon Adsorbing Layer Using a Stacked-Type Cell

    213th ECS Meeting  2008 

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  • #1512 Recyclable Electron Transfer System: Viologen/Pd-Promoted Reductive Coupling of Aryl Halides in Ionic Liquid

    214th ECS Meeting  2008 

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  • 水中で機能する有機還元剤の調製と芳香族ハロゲン化物の還元的カップリング反応

    第32 回有機電子移動化学討論会, P11  2008 

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  • 活性炭吸着相を反応場とする電解還元脱ハロゲン化

    電気化学会75回大会  2008 

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  • 活性炭吸着相を反応場とする芳香族ハロゲン化物の電解還元脱ハロゲン化-積層型セルの開発

    日本化学会第88春季大会  2008 

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  • O/W ナノエマルション系における両親媒性アルコールの電解酸化

    日本化学会第88春季大会  2008 

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  • ビオロゲンを基本骨格とする有機還元剤の循環系の開発

    日本化学会第88春季大会  2008 

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  • 還元型ビオロゲンを電子プールとする芳香族ハロゲン化物の水中二量化反応

    日本化学会第88春季大会  2008 

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  • P-27 活性炭吸着相を反応場とする電解還元脱ハロゲン化

    化学道場 2007  2007 

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  • ビオロゲンをメディエータとするハロゲン化アリールの電解還元二量化

    2007 年日本化学会西日本大会, 1PA-51  2007 

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  • ビオロゲン/Pd 触媒を用いるハロゲン化アリールの電解還元二量化反応

    第54 回有機金属化学討論会, PB241  2007 

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  • 活性炭吸着相を反応場とする電解還元脱ハロゲン化

    2007 年電気化学秋季大会, 1E20  2007 

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  • 1E20 活性炭吸着相を反応場とする電解還元脱ハロゲン化

    2007年電気化学秋季大会  2007 

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  • SIL-18 Electron Pool (V0): Generation by Electroreduction of Viologen (V2+) & Promotion of Reductive Homo-Coupling of Aryl Halides

    ISOETC2007 (Yokohama JAPAN)  2007 

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  • P-25 6,6-ジプロモペナムから調製したマグネシウムエノラートのアルドール反応における立体制御

    化学道場 2007  2007 

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  • Electrooxidation of Alcohols Mediated by N-Oxyl Immobilized in Ionic Liquid

    2nd International Congress on Ionic Liquids (Coil-2)  2007 

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  • P27 活性炭吸着相を反応場とする芳香族ハロゲン化物の電解還元脱ハロゲン化反応

    第31回有機電子移動討論会  2007 

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  • O16 還元型ビオロゲン/遷移金属触媒を用いたハロゲン化アリールおよびアルケニルの還元的カップリング反応

    第31回有機電子移動討論会  2007 

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  • 474TEMPO-Mediated Electrooxidation of Amphiphilic Alcohols in Nano-Particle Disperse Water Systems

    ECS 211th ECS Meeting  2007 

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  • 2J06 活性炭布に吸着した芳香族塩素化物の電解還元・脱塩素化反応

    電気化学会第74回大会  2007 

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  • 1J05 還元型ビオロゲン (V0)/Pd cat. 複合系を用いるハロゲン化アリールのホモカップリング反応

    電気化学会第74回大会  2007 

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  • 2D6-36 カルバペナム系抗生物質の汎用中間体 (3S, 4R)-3-[1(R)-ヒドロキシエチル]-4-クロロ-2-アゼチジノンの立体選択的な合成へのアプローチ

    日本化学会第87春季年会(2007)  2007 

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  • 2D6-35 6,6-ジブロモペニシラネートから調製したマグネシウムエノラートの反応における立体制御

    日本化学会第87春季年会(2007)  2007 

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  • 1D6-34 還元型ビオロゲン (V0)/Pd cat. 複合系を用いるハロゲン化アリールのホモカップリング反応。適用範囲の探索

    日本化学会第87春季年会(2007)  2007 

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  • 1D6-33 還元型ビオロゲン (V0) の電解合成およびその反応における Mg イオンの効果

    日本化学会第87春季年会(2007)  2007 

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  • 1D6-32 活性炭吸着相の芳香族ハロゲン化物の電解還元脱ハロゲン化反応

    日本化学会第87春季年会(2007)  2007 

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  • PP-31 TEMPO-Mediated Electrooxidation of Amphiphilic Alcohols in Nano-Particle Disperse Water Systems

    ISOETC2007 (Yokohama JAPAN)  2007 

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  • 3J4-05 両親媒性アルコールの水中での電解酸化の反応機構

    日本化学会年会第86春季年会 (2006)  2006 

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  • 3J4-04 両親媒性TEMPOをメディエータとするアルコールの水系電解酸化

    日本化学会年会第86春季年会 (2006)  2006 

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  • PB125 還元型ビオロゲンを電子プールとするハロゲン化アリールのホモカップリング反応

    第 53 回 有機金属化学討論会  2006 

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  • 水の中で電気を流して欲しいものつくる!〜水中でのナノ構造体の形成とその働き

    2006年度岡山大学大学院自然科学研究科高大連携・一般公開高校生・大学院生による研究紹介と交流の会- サステイナブル社会をめざす自然科学にふれてみよう-, L-12  2006 

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  • 水の中で電気を流して欲しいものつくる!〜水中でのナノ構造体の形成とその働き

    2006年度岡山大学大学院自然科学研究科高大連携・一般公開 高校生・大学院生による研究紹介と交流の会 - サステイナブル社会をめざす自然科学にふれてみよう - L-12  2006 

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  • 両親媒性アルコールの水系電解酸化-動的光散乱によるナノ粒子分散系の解析

    第 30 回有機電子移動化学討論会  2006 

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  • 水系有機電解合成-電解媒体の循環利用へのアプローチ

    第 30 回有機電子移動化学討論会  2006 

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  • TEMPO-Mediated Electro-oxidaiton of Alcohols in Water:Hydrophilic & Hydrophobic Interactions

    209th ECS Meeting  2006 

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  • Octylviologen Bis(trifluoromethanesulf)imide [C8V2+][Tf2N-]2 as a Recyclable Organic Reductant

    209th ECS Meeting  2006 

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  • ILA11 Reductive Homo- and Cross-Coupling of Allyl- and Propargylpalladium Species with Tetrakis(dimethylamino)ethylene as an Electron Source

    The 8th International Symposium on Organic Reactions  2006 

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  • OralB2 Synthesis of 2’,3’-Dideoxynucleosides: N-Glycosylation of 1-Thio-2,3-dideoxyglycosides through C-S Bond Cleavage

    The 8th International Symposium on Organic Reactions  2006 

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  • 3J4-52 Pd/TDAE 系における炭素-炭素結合生成反応. 酢酸プロパルギルとアルデヒドとの反応

    日本化学会年会第86春季年会 (2006)  2006 

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  • 3J4-51 還元型ビオロゲンを電子プールとするハロゲン化アリールのホモカップリング反応

    日本化学会年会第86春季年会 (2006)  2006 

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  • 両親媒性アルコールの水系電解酸化-動的光散乱によるナノ構造体の解析

    有機電子移動化学若手研究討論会  2006 

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  • PB-080 Pd-catalyzed Reductive Coupling of Ar?Br with Viologen as Recyclable Organic Reductant

    The 10th International KYOTO Conference on New Aspects of Organic Chemistry  2006 

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  • P22 両親媒性アルコールの水系電解酸化-動的光散乱によるナノ粒子分散系の解析

    第22回若手化学者のための化学道場  2006 

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  • 2N06 ビオロゲンの電解還元による電子プールの調製と反応

    2006 年電気化学秋季大会  2006 

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  • Pd-TDAE 複合レドックス系におけるノルボルネン誘導体とハロゲン化アリールとの3分子連結反応

    日本化学会第85春季年会  2005 

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  • A Prominent Access to Electrooxidation of Alcohols in Water

    1st International Symposium on Organic Electron Transfer Chemistry derected toward Organic Synthesis (ISOETC-2005), ISL22  2005 

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  • N-Oxyl-Mediated Electrooxidation of Amphiphilic Alcohols in Water

    The 56th Annual Meeting of the International Society of Electrochemistry, 6-002-O  2005 

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  • 両親媒性アルコールの水系電解酸化における疎水 vs. 親水性相互作用

    第29回エレクトロオーガニックケミストリー討論会, P2  2005 

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  • TDAE を電子源に用いる 2,2-ジブロモペニシリン誘導体の還元的分子変換

    第29回エレクトロオーガニックケミストリー討論会, P1  2005 

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  • 1-チオ-2,3-デオキシ糖の酸化的 N-グリコシル化反応の立体化学

    第29回エレクトロオーガニックケミストリー討論会, O9  2005 

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  • Synthesis of Water-Soluble PEG-TEMPO and Its Application to the Electrooxidation of Alcohols in Water

    ECS 207th Meeting - Quebec City, Canada, 1445  2005 

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  • Carbon-Carbon Bond-Making Reactions in Transition Metal Catalysts/TDAE System

    1st International Symposium on Organic Electron Transfer Chemistry derected toward Organic Synthesis (ISOETC-2005), ISL28  2005 

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  • 両親媒性アルコール類の水中電解酸化反応

    日本化学会第85春季年会 (2005), 3D4-35  2005 

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  • 遷移金属-TDAE 複合レドックス系を用いる炭素-炭素結合生成反応

    日本化学会第85春季年会 (2005), 3D4-28  2005 

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  • 遷移金属触媒を反応中心とする多重レドックス系を用いる分子変換反応の開発

    有機合成化学協会中国四国支部 支部奨励賞受賞講演会ならびに特別招待講演会  2005 

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  • 固体粒子/NaOCl 水溶液分散系におけるアルコールの酸化反応

    第28 回エレクトロオーガニックケミストリー討論会, P18  2004 

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  • 水を媒体とするアルコールの電解酸化

    第28 回エレクトロオーガニックケミストリー討論会, P17  2004 

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  • N-オキシル固定化イオン性液体を媒体とするアルコールの電解酸化

    第28 回エレクトロオーガニックケミストリー討論会, O32  2004 

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  • Electro-oxidation of Alcohols in N-Oxyl-Immobilized Ionic Liquids -Approach to a Toatlly Closed System

    205th Meeting of The Electrochemical Society, 2004, Abstract No. 797.  2004 

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  • ペニシリン誘導体の電解酸化開裂による4-置換アゼチジノン誘導体の合成

    日本化学会第84 春季年会 4E1-13  2004 

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  • N-オキシル固定化ポリマー粒子分散-水系における次亜塩素酸ナトリウムによるアルコールの酸化

    日本化学会第84 春季年会 4E1-04  2004 

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  • N-Oxyl-Mediated Electrooxidation of Alcohols in Water

    2004 Joint International Meeting: 206th Meeting of The Electrochemical Society (ECS) and 2004 Fall Meeting of The Electrochemical Society of Japan (ECSJ)  2004 

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  • N-オキシル誘導体をメディエーターとする水溶性アルコールの水系電解酸化

    日本化学会第84 春季年会 4E1-03  2004 

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  • Pd/TDAE 複合レドックスを用いるハロゲン化アリールのオレフィンとのカップリング反応

    日本化学会第84 春季年会 3E1-13  2004 

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  • アルミニウムを電子源とする複合金属レドックス系におけるジイミンの還元的分子内環化反応

    日本化学会第84 春季年会 3E1-11  2004 

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  • テトラキス(ジメチルアミノ) エチレン-遷移金属触媒電子移動系を用いる有機合成-

    第20 回若手化学者のための化学道場〜  2004 

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  • N-オキシル固定化シリカゲル/Aq. NaOCl-分散系における1,2-ジオールの酸化

    日本化学会第83春季年会(2003)講演予稿集Ⅱ,939頁,3G1-13  2003 

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  • (DHQD)2PHAL固定化シリカゲル分散-水系を用いるオレフィンの不斉ジヒドロキシル化反応

    日本化学会第83春季年会(2003)講演予稿集Ⅱ,1003頁,2G4-28  2003 

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  • 修飾ポリ(エチレン-co-アクリル酸)粒子を分散した水中でのアルコールの電解酸化

    日本化学会第83春季年会(2003)講演予稿集Ⅱ,927頁,1G1-23  2003 

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  • N-オキシルをメディエーターに用いるシリカゲル分散-水系でのアルコールの電解酸化.シリカゲルの化学修飾の効果

    日本化学会第83春季年会(2003)講演予稿集Ⅱ,927頁,1G1-22  2003 

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  • Electrooxidation of alcohols in an N-oxyl immobilized rigid polymer particles disperse water system

    The 203rd Meeting of The Electrochemical Society  2003 

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  • Synthesis of water-soluble N-oxyl derivative and it's application to the electrooxidation of alcohols in water

    The 203rd Meeting of The Electrochemical Society  2003 

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  • イオン性液体を反応場とするcat. Pd/TDEAを用いた芳香族ハロゲン化物の還元的二量化反応

    日本化学会第83春季年会(2003)講演予稿集Ⅱ,1037頁,3G5-30  2003 

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  • Pd/TDAE錯体を用いるアリルエステルの脱保護

    日本化学会第83春季年会(2003)講演予稿集Ⅱ,1037頁,3G5-29  2003 

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  • シリカゲル分散-水系でのオレフィンのジヒドロキシル化反応 -カラムフローシステムへの展開-

    日本化学会第83春季年会(2003)講演予稿集Ⅱ,939頁,3G1-14  2003 

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  • イオン性液体を反応場とするcat. Pd/TDAEを用いた芳香族ハロゲン化物の還元的二量化反応

    2003年日本化学会西日本大会講演予稿集,283頁,2H16  2003 

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  • テトラキス(ジメチルアミノ)エチレン/遷移金属触媒複合レドックス系による炭素-炭素結合生成反応の開発

    2003年日本化学会西日本大会講演予稿集,271-272頁,2H04  2003 

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  • テトラキス (ジメチルアミノ) エチレン/遷移金属触媒複合レドックス系による炭素-炭素結合生成反応の開発

    2003年日本化学会西日本大会  2003 

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  • テトラキス(ジメチルアミノ)エチレン-遷移金属触媒を用いる電子移動反応

    第27回エレクトロオーガニックケミストリー討論会講演予稿集,56-57頁,講演番号27  2003 

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  • 水系有機電解を基盤とする廃棄物ゼロ反応システム開発へのアプローチ

    電気化学会創立70周年記念大会講演要旨集(2003),203頁,講演番号1I07  2003 

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  • Asymmetric dihydroxylation of olefins in a chiral ligand-immobilized silica-gel/water disperse system

    The 203rd Meeting of The Electrochemical Society  2003 

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  • イオン性液体を反応溶媒とするアルコールの電解酸化-完全クローズド電解システムへのアプローチ-

    2003年日本化学会西日本大会講演予稿集,284頁,2H17  2003 

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  • Electrooxidation of alcohols in a polymer particles disperse water system. Totally closed electrolysis system

    53rd Annual Meeting of the International Society of Electrochemistry  2002 

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  • N-Oxyl-mediated electrooxidation of alcohols in silica gel-aqueous NaOCl disperse systems (ex-cell method). A column-flow system

    The 201st Meeting of The Electrochemical Society  2002 

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  • Ni/Pb複合金属レドックスをメディエータとする3-置換セフェムの電解還元.ノルセファロスポリンの合成.

    日本化学会第79春季年会  2001 

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  • シリカゲル分散-水系電解.N-オキシル固定化シリカゲルを用いるアルコールの電解酸化

    日本化学会第79春季年会  2001 

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  • TDAE/Ni/Crレドックス系におけるアルデヒドのアルキニル化反応

    日本化学会第79春季年会  2001 

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  • 酸化還元活性基を有する光学活性パラジウム錯体の合成とその電気化学的挙動

    日本化学会第79春季年会  2001 

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  • N-オキシル/トリアリールアミン複合レドックス化合物の合成とその電気化学的挙動

    日本化学会第79春季年会  2001 

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  • N-オキシル修飾 PBZT の合成及び PBZT 分散-水系でのアルコールの電解酸化

    日本化学会第79春季年会  2001 

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  • N-オキシル修飾ポリエチレンの合成及びポリエチレン分散-水系でのアルコールの電解酸化

    日本化学会第79春季大会  2001 

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  • シリカゲル分散-水系電解.遷移金属をメディエーターとするオレフィンの酸化

    日本化学会第79春季大会  2001 

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  • シリカゲル分散-水系電解. アルコールの電解酸化反応におけるシリカゲルの化学修飾効果

    日本化学会第79春季年会  2001 

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  • Electrooxidation of alcohols in an aqueous N-oxyl- immobilized silica gel disperse system

    The 200th Meeting of The Electrochemical Society  2001 

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  • Synthesis and Electrochemical Properties of N-Oxyl/Triarylamine Combined Redox Materials

    200th Meeting of the Electrochemical Society  2001 

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  • Products-Selectivity of Reductive Carbon-Carbon Bond Formation in Transition Metal Catalyst/Tetrakis(dimethylamino)ethylene (TDAE) Systems

    International Symposium on Integrated Synthesis 2001  2001 

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  • Polymer supported N-oxyl mediated electrooxidation of alcohols in aqueous NaBr/NaHCO3

    The 199th Meeting of The Electrochemical Society  2001 

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  • 水溶性酸化剤を用いたシリカゲル分散-水系におけるオレフィンの酸化反応

    グリーン・サステイナブルケミストリーシンポジウム2001よこはま  2001 

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  • 多機能化されたシリカゲルを用いるアルコールの水系電解酸化反応

    日本化学会中国四国支部・同九州支部合同大会  2001 

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  • Pd/テトラキス(ジメチルアミノ)エチレン複合系におけるハロゲン化アリールの還元的二量化

    日本化学会中国四国支部・同九州支部合同大会  2001 

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  • 剛直性ポリマー粒子分散水系におけるアルコールの電解酸化

    2001年電気化学秋季大会  2001 

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  • 環境調和型有機電解合成を目指して-分散水系電解法の開発

    日本化学会第80秋季年会  2001 

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  • Carbon-carbon bond formation using TDAE/transition metal system

    2000 International Chemical Congress of Pacific Basin Societies  2000 

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  • Multi-redox promoted reductive coupling of aryl halides. TDAE as an electron source

    2000 International Symposium on Organic Reactions-Tokyo (2000 ISOR-Tokyo)  2000 

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  • マルチレドックス系を用いる炭素-炭素結合形成反応の開発

    第35回有機反応若手の会  2000 

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  • Carbon-carbon bond formation using TDAE/transition metal system

    The Eighth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-8)  2000 

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  • Synthesis of 3-akenyl-D3-cephems through reductive coupling of 3-substituted D3- cephems with alkenyl halides in an Al/PbBr2/ NiBr(bpy) system

    The Eighth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-8)  2000 

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  • Carbon-carbon bond formation using tetrakis(dimethyl-amino)ethylene (TDAE) as reductant/mediator

    The 197th Meeting of the Electrochemical Society in Toronto  2000 

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  • N-Oxyl mediated oxidation of alcohol in an aqueous silica gel disperse electrolysis system

    The 197th Meeting of the Electrochemical Society in Toronto  2000 

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  • Electrochemical re-generation of chromium(II). A catalytic Nozaki- Hiyama-Kishi reaction

    The 195th Meeting of The Electrochemical Society  1999 

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  • Generation and reaction of o-quinonemethide imine by electrolysis of o-[3,5-di(t-butyl)- 4-methoxyphenylsul- fenyl]methylaniline derivatives

    The 195th Meeting of The Electrochemical Society  1999 

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  • 触媒的野崎-檜山反応の開発

    有機電気化学研究会第二回セミナー  1999 

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  • Carbon-carbon bond formation in an Ni/Cr/TDAE redox system

    The 9th Tohwa University International Symposum on Chemistry into the 21st Century  1999 

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Industrial property rights

  • triazatriphosphorine by ammonolysis of hexachlorocyclotriphosphazene or diaminotetrachlorocyclotriphosphazene

    Tanaka, Hideo; Kuroboshi, Manabu; Murakami, Masaki

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    Applicant:Tanaka, Hideo; Kuroboshi, Manabu; Murakami, Masaki

    Application no:JP2019123693 A  Date applied:2019.7.25

    Announcement no:JP2019123693 A  Date announced:2019.7.25

    Rights holder:Tanaka, Hideo; Kuroboshi, Manabu; Murakami, Masaki

  • Method for manufacturing cyclic chlorophosphazene trimer

    Murakami, Masaki; Tanaka, Hideo; Kuroboshi, Manabu

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    Applicant:Murakami, Masaki; Tanaka, Hideo; Kuroboshi, Manabu

    Application no:WO2019049872  Date applied:2019.3.14

    Announcement no:WO2019049872  Date announced:2019.3.14

  • Method for the preparation of cyclic aryloxyphosphazene

    Tanaka, Hideo; Kuroboshi, Manabu; Murakami, Masaki

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    Applicant:Tanaka, Hideo; Kuroboshi, Manabu; Murakami, Masaki

    Application no:JP2019218288 A  Date applied:2019

    Announcement no:JP2019218288 A   Date announced:2019.12.26

    Rights holder:Tanaka, Hideo; Kuroboshi, Manabu; Murakami, Masaki

Awards

  • 岡山工学振興会科学技術賞

    2001  

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    Country:Japan

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