Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/j.dyepig.2023.111916

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Authorship：Lead author,　Corresponding author   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Abstract

Indirect electrolysis method using appropriate mediators enables numerous chemical reactions. The general principles of mediators were described herein with a particular focus on non‐transition metal mediators. Recent representative examples of bond formation reactions by indirect electrolysis are summarized and discussed here.

DOI： 10.1002/ejoc.202300835

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Electrochemical Society of Japan  

DOI： 10.5796/electrochemistry.23-67078

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Electrochemical Society of Japan  

DOI： 10.5796/electrochemistry.23-67079

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.orglett.3c01914

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

Electrochemical dehydrogenative C-O bond formation for the synthesis of sultones was achieved. In the presence of K2CO3 and H2O, constant current electrolysis of [1,1'-biphenyl]-2-sulfonyl chloride afforded an aryl-fused sultone quantitatively. Under the optimized conditions, a variety of sultone derivatives were obtained. Control experiments suggest that the electrochemical oxidation of the sulfonates generated in situ would afford sulfo radical intermediates.

DOI： 10.1021/acs.orglett.3c01062

PubMed

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Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

Abstract

An electrochemical cross-coupling reaction between arylboronic esters and aryllithiums was developed. The presence of Br– in the electrolyte was found to be essential for the reaction. NaBr was chosen as the electrolyte for its inexpensiveness and abundance, and also acted as a halogen mediator. The reaction proceeded under mild conditions to afford biaryls.

DOI： 10.1055/a-2034-9821

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.oprd.2c00267

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Authorship：Lead author,　Corresponding author   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.orglett.2c03574

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Oxford University Press (OUP)  

DOI： 10.1246/cl.220368

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Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Beilstein Institut  

Electrochemical hydrogenation of enones using a proton-exchange membrane reactor is described. The reduction of enones proceeded smoothly under mild conditions to afford ketones or alcohols. The reaction occurred chemoselectively with the use of different cathode catalysts (Pd/C or Ir/C).

DOI： 10.3762/bjoc.18.107

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Other Link： https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-18-107.pdf

Language：English   Publishing type：Research paper (scientific journal)   Publisher：MDPI AG  

Five triphenyltriphenylamines with various substituents were investigated as precursors for near-infrared absorbing materials. Cyclic voltammetry (CV) studies showed that they all give stable radical cations in solution. The radical cations obtained by one-electron chemical oxidation of these compounds show strong absorption in the near-infrared region, and the position of the absorption is strongly influenced by the substituent. DFT (density functional theory) calculations suggest that the introduction of stronger electron-donating substituents would result in a smaller HOMO–SOMO energy gap and thus a larger long wavelength shift, which is consistent with the experimental results. On the other hand, strong electron-withdrawing substituents increase the HOMO–SOMO energy gap, resulting in a short wavelength shift. The position of the near-infrared absorption peak of the triphenylamine radical cation can be controlled to the longer or shorter wavelength direction depending on the substituent. A molecular design of near-infrared absorbing dyes utilizing the electronic effects of substituents is described.

DOI： 10.3390/colorants1030021

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/cl.220112

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

DOI： 10.3390/colorants1020014

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

Cyanosilylation of carbonyl compounds provides protected cyanohydrins, which can be converted into many kinds of compounds such as amino alcohols, amides, esters, and carboxylic acids. In particular, the use of trimethylsilyl cyanide as the sole carbon source can avoid the need for more toxic inorganic cyanides. In this paper, we describe an electrochemically initiated cyanosilylation of carbonyl compounds and its application to a microflow reactor. Furthermore, to identify suitable reaction conditions, which reflect considerations beyond simply a high yield, we demonstrate machine learning-assisted optimization. Machine learning can be used to adjust the current and flow rate at the same time and identify the conditions needed to achieve the best productivity.

DOI： 10.1021/acs.joc.1c01242

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/j.dyepig.2021.109929

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Authorship：Lead author,　Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/tcr.202100033

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Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/tcr.202100033

Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

The first Cu-catalyzed dehydrogenative C-O cyclization for the synthesis of furan-fused thienoacenes is described. A variety of heteroacenes including a thieno[3,2-b]furan or a thieno[2,3-b]furan skeleton were synthesized by intramolecular C-H/O-H coupling. The use of a mixed solvent of N-methyl-2-pyrrolidone, ethylene glycol monomethyl ether, and toluene was essential for suppressing side reactions and efficiently promoting the reaction. Double C-O cyclization was also conducted to afford highly π-expanded furan-fused thienoacenes.

DOI： 10.1021/acs.orglett.1c01256

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PubMed

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/cl.200809

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.orglett.0c03956

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

<p>4,4′-Bibenzo[<italic>c</italic>]thiophene <bold>4,4′-BBT</bold> and its silyl-substituted derivatives <bold>1,1′-Si-4,4′-BBT</bold> and <bold>1,1′,3,3′-Si-4,4′-BBT</bold> have been designed and developed as new π-building blocks.</p>

DOI： 10.1039/d1ra01189h

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Publishing type：Research paper (scientific journal)   Publisher：The Japan Institute of Heterocyclic Chemistry  

DOI： 10.3987/com-21-14433

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Authorship：Lead author,　Corresponding author   Language：English   Publisher：Georg Thieme Verlag {KG}  

<jats:title>Abstract</jats:title><jats:p>An electrochemical single-electron-transfer reaction is a promising method to generate reactive radical species in organic synthesis. One-electron oxidation of a neutral compound gives a radical cation, which usually breaks down into a radical and a cationic species; conversely, one-electron reduction of a neutral compound affords a radical anion, which forms a radical and an anionic species. The radical species generated in this way can be used for a variety of transformations. In this chapter, selected recent electrochemical transformations that involve electrogenerated radical species are collected and described.</jats:p>

DOI： 10.1055/sos-sd-233-00170

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Oxford University Press (OUP)  

Abstract

A method for the selective synthesis of 9-substituted fluorenols (FOLs) was developed by suppressing intermolecular cyclization and promoting intramolecular C–H functionalization. This protocol was applied to the synthesis of heteroring-fused FOLs. Further, the obtained FOLs were converted to fulvenes by dehydration.

DOI： 10.1246/cl.200807

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

A one-pot procedure for the synthesis of thienyl thioethers is described. Several thienyl thioethers were synthesized by a TfOH-promoted Friedel-Crafts-type cyclization, a subsequent nucleophilic attack by an arenethiol, and dehydration. This protocol was successfully applied to the synthesis of thienoacene derivatives by using a Pd-catalyzed dehydrogenative cyclization.

DOI： 10.1055/s-0040-1707280

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：International Union of Crystallography (IUCr)  

In the title molecule, C₄₈H₃₃N, the central N atom shows no pyramidalization, so that the N atom and the three C atoms bound to the N atom lie almost in the same plane. The three <italic>para</italic>-phenylene rings bonded to the N atom are in a propeller form. All of the naphthalene ring systems are slightly bent. In the crystal, molecules form an inversion dimer, through two pairs of C—H...<italic>π</italic> interactions, which further interacts with the adjacent dimer <italic>via</italic> another two pairs of C—H...<italic>π</italic> interactions, forming a column structure along the <italic>a</italic> axis. There are no significant interactions between these column structures.

DOI： 10.1107/s2056989020012529

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

DOI： 10.1246/cl.200161

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Publishing type：Research paper (scientific journal)   Publisher：Wiley  

DOI： 10.1002/ange.202001149

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

A 1,10-phenanthroline-promoted cyanation of aryl iodides has been developed. 1,10-Phenanthroline worked as an organocatalyst for the reaction of aryl iodides with tetraalkylammonium cyanide to afford aryl cyanides. A similar reaction occurred through an electroreductive process.

DOI： 10.1055/s-0037-1611793

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society ({ACS})  

The first synthesis of dithieno-1,2-oxaborine derivatives was achieved via iodide-mediated or iodide-catalyzed demethylation of 3-methoxy-2,2'-bithiophene and subsequent C-H borylation. A wide variety of thiophene-fused oxaborines could be synthesized by the procedure.

DOI： 10.1021/acs.orglett.9b00485

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

Abstract

An efficient enantioselective acyl migration reaction of furanyl carbonates was developed to construct all‐carbon quaternary stereogenic centers. In some cases, the reactions required only 0.05 mol % (minimum 500 ppm) of catalyst and showed a high turnover frequency value (TOF; 3640 h⁻¹). Multigram‐scale reactions (10 grams) also proceeded with high enantioselectivity (&gt;99:1 e.r.) in quantitative yield. The catalyst was robust and easily recovered in 98 % yield. A wide range of functional groups were tolerated (15 examples, &gt;98 % yield, up to &gt;99:1 e.r.), and a variety of optically active 3,3′‐disubstituted benzofuranone derivatives, which are useful intermediates for the synthesis of natural products and pharmaceuticals, were efficiently obtained. Control experiments on the catalyst structure (e.g., catalyst 1 a vs. 1 a′ and 1 a′′) and computational calculations revealed that both the catalytic activity and enantioselectivity should be enhanced by hydrogen bonding between catalyst and substrate. Moreover, this system was applied to the challenging γ‐selective acyl migration reaction of furanyl carbonates with high γ‐selectivity and high enantioselectivity (α:γ=10:90, 95:5 e.r.).

DOI： 10.1002/chem.201806050

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Publishing type：Research paper (scientific journal)   Publisher：Oxford University Press (OUP)  

DOI： 10.1246/cl.180697

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

The first synthesis of dithieno[3,2-b:2',3'-e][1,4]azaborinine (DTAB) derivatives has been achieved by Buchwald-Hartwig coupling and subsequent Friedel-Crafts-type C-H borylation. A facile method for further pi-extension of DTAB was also developed via stannylation and subsequent Kosugi-Migita-Stille cross-coupling reaction. The fundamental properties of DTAB derivatives were also investigated.

DOI： 10.1021/acs.orglett.8b03316

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

Efficient syntheses of benzodithienofuran (BDTF; [1]benzothieno[3,2-b]thieno[2,3-d]furan) and benzodithienothiophene (BDTT; [1]benzothieno[3,2-b]thieno[2,3-d]thiophene) were achieved by the combination of an addition-elimination reaction, reduction, and Pd-catalyzed dehydrogenative cyclization. We also achieved the synthesis of pi-ex- tended BDTF and BDTT derivatives through the use of coupling reactions. The detailed physical properties of these compounds were investigated. The newly synthesized BDTFs exhibited strong fluorescence compared with BDTTs. 2,2'-Bis([1]benzothieno[3,2-b]thieno[2,3-d]furan) (BBTTF) exhibited p-type organic field-effect transistor (OFET) properties.

DOI： 10.1002/ajoc.201800270

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society ({ACS})  

A dynamic kinetic resolution (DKR) of azlactones in the presence of benzoic acid and a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1i having two amide groups at the 3,3'-positions of a binaphthyl unit is developed. The reaction proceeded smoothly with a wide range of azlactones to provide alpha-amino acid derivatives with good to high enantiomeric ratios (er's). A multigram-scale reaction (2.5 g) for the DKR of azlactone 2d was also demonstrated, and the resulting product was converted to unnatural alpha-amino acid 6d'.

DOI： 10.1021/acs.orglett.8b01960

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Authorship：Lead author   Language：English   Publisher：American Chemical Society  

Recent advances in electro-organic chemistry involving miniaturization, integration, and combinatorial chemistry were reviewed. Microelectrode array technology for site-selective electro-organic reactions and addressable libraries provides a direct and unlabeled method for measuring small-molecule-protein interactions. Electrochemical systems using solid-supported bases and acids ("site separation") can realize electrolysis without the addition of supporting electrolytes. Well-designed "bipolar electrodes" have enabled the production of patterned gradient polymer brushes and microfibers. For the display of combinatorial organic electrochemistry, batch and flow electrolysis systems for the optimization and screening of electro-organic reactions as well as the building of chemical libraries for organic compounds are described.

DOI： 10.1021/acs.chemrev.7b00532

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Chemical Society of Japan  

Cu/Fe-cocatalyzed cross-coupling reactions between 3-bromobenzo[b]thiophene and hydroxyaryls are described herein. The combination of Cu and Fe catalysts is important for the progress of the reactions, and the use of triphenylphosphine oxide as a ligand suppresses the dehalogenation of 3-bromobenzo[b]thiophene, and promptly facilitates the reaction. The obtained aryl benzo[b]thienyl ethers can be converted to pextended thienobenzofuran derivatives via Pd-catalyzed dehydrogenative cyclizations.

DOI： 10.1246/cl.180425

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Beilstein-Institut Zur Forderung der Chemischen Wissenschaften  

In this study, six-membered N-acyliminium ions were generated by the “indirect cation pool” method and reacted with several nucleophiles. These reactions afforded disubstituted piperidine derivatives with high diastereoselectivities and good to excellent yields. The conformations of the obtained N-acyliminium ions were studied by low temperature NMR analyses and DFT calculations and were found to be consistent with the Steven’s hypothesis.

DOI： 10.3762/bjoc.14.100

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Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier B.V.  

In this study, recent advances in electro-organic chemistry based on combinatorial approaches are reviewed. As examples of combinatorial organic electrosynthesis, some batch and flow electrolysis systems for the screening and optimization of electro-organic reactions are described along with the construction of chemical libraries of organic compounds.

DOI： 10.1016/j.coelec.2017.10.026

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

The reaction of silyl dienol ether of gamma-pyrone with dimethyl acetylenedicarboxylate (DMAD) gives the regioselective insertion product in 66% yield. This DMAD-insertion reaction is thought to include a three-step sequence: (1) thermal [2+2]-type cycloaddition reaction of silyl dienol ether of gamma-pyrone with DMAD, (2) ring-opening electrocyclic reaction of the cyclobutene skeleton, and (3) hydrolysis of the silyl dienol ether. The present reaction proceeds under mild conditions without any catalysts or heating. In addition, the [2+2]-type cycloaddition reaction proceeds regioselectively at the C3-C4 double bond in the silyl dienol ether of gamma-pyrone.

DOI： 10.3987/COM-17-13820

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Language：Japanese   Publisher：電気化学会  

CiNii Article

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

We developed an acylative desymmetrization of meso-1,2-diols using a binaphthyl-based N,N-4-dimethylamino-pyridine (DMAP) derivative lh with tert-alcohol substituents. The reaction proceeds with a wide range of acyclic meso-1,2-diols and six-membered-ring meso-1,2-diols to provide a monoacylate selectively with a high enantiomeric ratio (er). Only 0.1 mol % of the catalyst facilitated the reaction within a short reaction time (3 h) to afford enantio-enriched monoacylated products in moderate to good yield. Several control experiments revealed that the tert-alcohol units of catalyst lh play a significant role in achieving high catalytic activity, chemoselectivity of monoacylation, and enantioselectivity.

DOI： 10.1021/acs.joc.7b00992

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

The synthesis of 3-benzo[b]thienyl 3-thienyl ether and its dehydrogenative cyclization leading to benzodithienofuran (BDTF; [1]benzothieno[3,2-b]thieno[2,3-d]furan) are described for the first time. Further transformation of BDTF to more p-extended BDTF derivatives and their fundamental physical properties are also studied.

DOI： 10.1021/acs.orglett.7b00969

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/acs.orglett.7b00878

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

Abstract

An extremely efficient acylative kinetic resolution of d,l‐1,2‐diols in the presence of only 0.5 mol% of binaphthyl‐based chiral N,N‐4‐dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert‐alcohol unit(s) of the catalyst and the 1,2‐diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2‐diols with high selectivity factors. The kinetic resolution of d,l‐hydrobenzoin and trans‐1,2‐cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min).

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DOI： 10.1002/adsc.201700057

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Japan Institute of Heterocyclic Chemistry  

DOI： 10.3987/com-16-13614

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：GEORG THIEME VERLAG KG  

Facile synthetic methods for constructing naphthothiophenone and its -extended derivatives were developed. Naphthothiophenone and anthradithiophenedione were synthesized by the S-acylation of thiol to form chlorothioformate and subsequent Friedel-Crafts acylation. A bromination reaction of naphthothiophenone and its application to Suzuki-Miyaura cross-coupling was also carried out. The fundamental physical properties of these compounds were also investigated.

DOI： 10.1055/s-0035-1562470

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Other Link： http://orcid.org/0000-0002-6744-7136

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

We developed an acylative kinetic resolution of secondary carbinols using a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1d with tert-alcohol substituents. The reaction proceeded with a wide range of carbinols with moderate to high selectivity (s) (up to s = 79.5). Kinetic studies revealed that catalyst 1d was more catalytically active than the corresponding bis-methyl ether 1d' or DMAP. Hydrogen bonding between tert-alcohols of the catalyst and secondary carbinols was responsible for the enhanced reaction rate and high enantioselectivity.

DOI： 10.1246/bcsj.20160135

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Springer Science and Business Media LLC  

Abstract

Catalysts that can promote acyl transfer processes are important to enantioselective synthesis and their development has received significant attention in recent years. Despite noteworthy advances, discovery of small-molecule catalysts that are robust, efficient, recyclable and promote reactions with high enantioselectivity can be easily and cost-effectively prepared in significant quantities (that is, &gt;10 g) has remained elusive. Here, we demonstrate that by attaching a binaphthyl moiety, appropriately modified to establish H-bonding interactions within the key intermediates in the catalytic cycle, and a 4-aminopyridyl unit, exceptionally efficient organic molecules can be prepared that facilitate enantioselective acyl transfer reactions. As little as 0.5 mol% of a member of the new catalyst class is sufficient to generate acyl-substituted all-carbon quaternary stereogenic centres in quantitative yield and in up to 98:2 enantiomeric ratio (er) in 5 h. Kinetic resolution or desymmetrization of 1,2-diol can be performed with high efficiency and enantioselectivity as well.

DOI： 10.1038/ncomms11297

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Other Link： https://www.nature.com/articles/ncomms11297

Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

Bis(diaryl)-1,3-butadiynes bearing two amino moieties were easily synthesized by a sequential coupling reaction by using an electrochemical method. This sequential reaction consists of electrochemical oxidative homocoupling and Suzuki-Miyaura coupling. The fluorescence of the obtained bis(diaryl)-1,3-butadiynes is solvatochromic despite their symmetric linear structure and lack of a strong acceptor moiety.

DOI： 10.1002/ajoc.201500502

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Other Link： http://orcid.org/0000-0002-6744-7136

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

Iron oxide produced by iron-oxidizing bacteria, Leptothrix ochracea, (L-BIOX) obtained from a freshwater purification plant, Joyo City in Kyoto, Japan catalyzed Baeyer-Villiger oxidation with molecular oxygen in the presence of benzaldehyde at 25 degrees C more efficiently than usual iron compounds. L-BIOX can promote the reactions of various substrates to give the desired products in sufficient yields and was found to be reusable. Scanning transmission electron microscopy and Fe-57 Mossbauer spectroscopy revealed that no change of the surface structure of L-BIOX was observed even after four times of the recycling test and the oxidation state of iron in L-BIOX is trivalent before and after the oxidation of cyclohexanone. An investigation with analogous amorphous iron oxides which contain silicon revealed that the catalytic activity of L-BIOX might stem from a synergetic effect of iron and silicon in the structure. (C) 2015 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2015.10.057

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Other Link： http://orcid.org/0000-0002-6744-7136

Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

A method for the facile synthesis of ethene-bridged terthiophenes (EBTTs) in two steps has been developed. The first step is a double Sonogashira coupling between 3',4'-dibromo-2,2':5',2 ''-terthiophene and terminal alkynes to give dialkynylated terthiophenes, and the second step is a cyclization reaction to afford EBTTs. The fundamental physical properties of EBTTs were also studied.

DOI： 10.1021/acs.orglett.5b02417

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Other Link： http://orcid.org/0000-0002-6744-7136

Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

Chiral N,N-4-(dimethylamino)pyridine (DMAP) derivatives, which can be readily prepared by the Ugi multicomponent reaction in a one-pot manner, have been efficiently applied to the enantioselective Steglich rearrangement of oxindole derivatives to give the desired products bearing a quaternary carbon center in high yield (&gt;98% yield) and with high enantioselectivity (up to 99:1 er).

DOI： 10.1021/acs.orglett.5b02089

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Other Link： http://orcid.org/0000-0002-6744-7136

Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-V C H VERLAG GMBH  

Palladium-catalyzed domino CH/NH functionalization for the synthesis of novel nitrogen-bridged thienoacenes and 10H-benzo[4,5]thieno[3,2-b]indole derivatives from dihaloarene is reported. This domino sequence consists of initial CH functionalization of the benzo[b]thiophene moiety, followed by Buchwald-Hartwig coupling. This transformation is also useful for the synthesis of highly -extended compounds.

DOI： 10.1002/chem.201500897

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Authorship：Lead author   Language：English   Publisher：The Electrochemical Society of Japan  

DOI： 10.5796/electrochemistry.83.477

CiNii Article

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Other Link： https://jlc.jst.go.jp/DN/JLC/20011551902?from=CiNii

Authorship：Lead author   Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：Society of Synthetic Organic Chemistry  

An electrochemical method to synthesize cationic palladium complexes has been developed. Their counter anions could be changed readily by the electrolyte. The reaction could be incorporated into electro - oxidative palladium catalyzed reactions, such as Wacker-type reaction, homo -coupling of arylboronic acids, oxidative Sonogashira-type coupling, and Glaser - type coupling of terminal alkynes. These reactions exhibited a wide scope and a variety of products were obtained in high yields due to high activity of electrogenerated palladium species. We also developed site-selective sequential reactions by the integration of the electro - oxidative coupling reactions with non - electrochemical reactions. The reaction site could be controlled completely by the onloff application of electricity.

DOI： 10.5059/yukigoseikyokaishi.73.171

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/j.bmc.2014.07.047

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Georg Thieme Verlag KG  

DOI： 10.1055/s-0034-1378900

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

Abstract

The rate of the intramolecular Morita‐Baylis–Hillman (MBH) reaction is remarkably enhanced by the combination of catalytic amounts of a nucleophilic catalyst (4‐dimethylaminopyridine (DMAP), 4‐pyrrolidinopyridine (PPY), or PBu₃) and 1,3‐diphenyl‐2‐thiourea, and the desired MBH adducts are obtained in good to high yields within a few hours.

DOI： 10.1002/ajoc.201402001

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELECTROCHEMICAL SOC JAPAN  

An electro-reductive halogen-deuterium exchange reaction in CD3CN has been developed. Using 9-fluorenone as a mediator, the electro-reduction of several aryl halides proceeded smoothly to give the deuterated products selectively. A methylation reaction of aryl halides also proceeded under similar conditions. (C) The Electrochemical Society of Japan, All rights reserved.

DOI： 10.5796/electrochemistry.81.362

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELECTROCHEMICAL SOC JAPAN  

Electro-oxidative Wacker-type reaction has been developed in PEG/CH3CN thermomorphic biphasic system. The heterogeneous solution was turned into homogeneous solution with heating to 60 degrees C, and electro-oxidative Wacker-type reactions of alkenes bearing long alkyl chains proceeded smoothly to afford methyl ketones in good yields. The recycling of PEG phase containing Pd has also been achieved. (C) The Electrochemical Society of Japan, All rights reserved.

DOI： 10.5796/electrochemistry.81.347

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

The first synthesis of hexa(furan-2-yl)benzene derivatives is described. The RhCl3/i-Pr2NEt-catalyzed cyclotrimerization of di(furan-2-yl)acetylenes was an effective method for constructing hexa(furan-2-yl)benzene derivatives in good yields. Their π-extended derivatives were also synthesized by Suzuki-Miyaura coupling between hexakis(5-Bpinfuran-2-yl)benzene (Bpin = (pinacolato)boryl) and several aryl iodides. © 2013 American Chemical Society.

DOI： 10.1021/jo302652r

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

The kinetic resolution of secondary alcohols was examined by new chiral DMAP derivatives, which can readily be prepared by the Ugi multicomponent reaction in a one-pot operation. The initial screening of DMAP derivatives indicated that the catalyst bearing L-valine with an S configuration at the a-position of amide showed the best stereoselectivity factor. After the reaction conditions were optimized with (S,S)-4a in the kinetic resolution of secondary alcohols, various acyclic and cyclic secondary alcohols could be resolved with an s -factor of up to 12. © 2013 The Japan Institute of Heterocyclic Chemistry.

DOI： 10.3987/COM-12-12624

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/j.electacta.2012.03.130

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

An efficient and simple protocol for the kinetic resolution of secondary alcohols is presented. The new system is based on a combination of chiral Bronsted acid, DABCO, and acetyl chloride and gives various enantioenriched alcohols with selectivity factors up to 105.

DOI： 10.1021/ol301373x

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

The first synthesis of nitrogen-bridged terthiophenes (NBTTs) has been achieved by a tandem Buchwald-Hartwig coupling of 3,3',3 '', 4'-tetrabromo-2,2':5',2 ''-terthiophene. Several NBTT derivatives bearing aryl or alkyl moieties on the N-atoms could be synthesized. Their fundamental electrochemical characteristics and HOMO-LUMO levels were found to be influenced by the substituents on the N-atoms.

DOI： 10.1021/ol300887t

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

Site-selective sequential coupling reactions directed toward bis(diaryl)butadiynes are described. The reaction site could be controlled completely by the on/off application of electricity. The electro-oxidative homo-coupling of terminal alkynes (electricity ON) and the subsequent Suzuki-Miyaura coupling (electricity OFF) afforded bis(diaryl) butadiynes in high yields. The obtained 1,4-bis(diaryl)butadiynes could be converted to a 2,5-bis(diaryl)thiophene derivative, which exhibited blue fluorescence.

DOI： 10.1039/c2ob26567b

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：MDPI AG  

Diastereoselective Ugi reactions of DMAP-based aldehydes with alpha-amino acids and tert-butyl isocyanide were examined. The reactions of 4-(dimethylamino)-2-pyridine-carboxaldehyde with various alpha-amino acids afforded 2-substituted DMAP derivatives with low diastereoselectivity. On the contrary, reactions with 4-(dimethylamino)-3-pyridine-carboxaldehyde delivered 3-substituted DMAP derivatives with moderate to high diastereoselectivity. The combination of alpha-amino acid and DMAP-based aldehyde is thus important to achieve high diastereoselectivity. Kinetic resolution of a secondary alcohol using a chiral DMAP derivative obtained through these reactions was also examined.

DOI： 10.3390/molecules16108815

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Carbene ligands bearing a pyridyl group and an ethylenedioxyl moiety were developed, and utilized as efficient ligands for the nickel-catalyzed Kumada-Tamao-Corriu coupling. A wide variety of aryl chlorides could be used for the cross-coupling reaction with aryl Grignard reagents to afford the corresponding products in high yields in short time.

DOI： 10.1246/cl.2011.936

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

An electro-oxidative method for generating silver acetylides from acetylenes with a Ag anode was developed. The reaction could be integrated into a Pd-catalysed electrochemical Sonogashira-type reaction. In the presence of the catalytic amount of Pd(OAc)(2) and 4-BzO-TEMPO, electro-generated silver acetylides reacted immediately with arylboronic acids to afford the corresponding coupling adducts in high yields.

DOI： 10.1039/c0cc02633f

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

Novel long-chain dialkyl fluorene-9,9-dicarboxylates were synthesized by treating fluorene with lithium diisopropylamide followed by alkyl chloroformates. The fluorene derivatives were readily electro-oxidized to form electroactive films on the Surface of a glassy carbon electrode. From the viewpoint of suitable potential window (from -2.5 to 1.5 V vs Ag/Ag(+)), cyclic voltammograms of the films indicated the electroactive properties of the fluorene derivatives that make them good candidates for electrochemical capacitor materials. (C) 2009 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2009.08.052

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

A facile electrooxidative method for synthesizing biaryls from arylboronic acids or arylboronic esters is described. In the presence of a catalytic amount of Pd(OAC)(2) and TEMPO, the electrooxidation of arylboronic acids or arylboronates gave the corresponding biaryls in moderate to excellent yields. (C) 2009 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2009.08.004

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Electrochemical Society of Japan  

DOI： 10.5796/electrochemistry.77.1002

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELECTROCHEMICAL SOC JAPAN  

Palladium/2,2,6,6-tetramethylpiperidine-1-oxyl (Pd/TEMPO) double-mediatory electrooxidative Wacker-type cyclization of 1 was developed. In a mixture solution of dioxane and water, the reaction efficiently proceeded at room temperature to give benzofuran derivative 2.

DOI： 10.5796/electrochemistry.76.859

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

Nickel pincer complex 1 was prepared by the treatment of nickel pincer 2 with AgBF(4). Cationic nickel pincer complex 1 was air-stable and easy to handle, and was successfully applied to Michael addition and Mizoroki-Heck reaction. (C) 2008 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2008.10.029

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/j.tetlet.2008.09.022

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/j.tet.2008.03.079

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Authorship：Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

In the presence of RhCl(3)center dot 3H(2)O and i-Pr(2)NEt, the cyclotrimerization of di(2-thienyl)acetylenes proceeded smoothly to afford hexa(2-thienyl)benzenes. CV analysis of the hexa(2-thienyl)benzenes showed that they may be useful as electroactive materials. (C) 2008 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2008.02.069

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DOI： 10.1016/j.tetlet.2007.10.088

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Oxford University Press (OUP)  

Abstract

RhCl3/amine was found to be an efficient catalyst for the cyclotrimerization of alkynes. The [2+2+2] cyclotrimerization of internal alkynes proceeded smoothly to afford hexa-substituted benzenes regioselectively in moderate to high yields.

DOI： 10.1246/cl.2007.998

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Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/ja069043r

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：The Electrochemical Society of Japan  

DOI： 10.5796/electrochemistry.75.54

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Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/ol061373t

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Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/j.tetlet.2006.05.060

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/j.tetlet.2005.10.114

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Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/ol051776d

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/ja047484+

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

DOI： 10.1002/1521-3773(20020916)41:18<3481::aid-anie3481>3.0.co;2-x

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/s0022-328x(02)01173-7

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/jo0163389

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Oxford University Press (OUP)  

Abstract

The Rh- and Pt-catalyzed hydrosilylations of olefin utilizing 2-pyridyl-, 3-pyridyl-, 4-pyridyl-, and phenyldimethylsilane are described. Whereas huge rate acceleration was observed with 2-PyMe2SiH in the Rh-catalyzed reaction, huge rate deceleration was observed with 2-PyMe2SiH and 4-PyMe2SiH in the Pt-catalyzed reaction.

DOI： 10.1246/cl.2001.1088

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/ja016790+

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DOI： 10.1002/1521-3757(20010618)113:12<2399::aid-ange2399>3.0.co;2-2

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley-Blackwell  

Facile addition of primary alkyl Gridnard reagents to vinylsilanes has been realized for the first time by exploiting the directing effect of a 2-pridyl group on silicon [Eq. (1)]. Three-component coupling reactions of a Grignard reagent, the vinylsilane, and an electrophile, followed by oxidative removal of the 2-pyridyldimethylsilyl group with H2O2 furnishes various secondary alcohols in excellent overall yields.

DOI： 10.1002/1521-3773(20010618)40:12<2337::AID-ANIE2337>3.0.CO;2-Q

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/jo015528g

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/ja002582q

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

DOI： 10.1021/jo990740u

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DOI： 10.1021/om9904394

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/s0040-4039(99)01028-x

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/s0040-4039(99)01027-8

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

DOI： 10.1016/s0040-4039(99)00474-8

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Publisher：The Electrochemical Society  

DOI： 10.1149/MA2020-01432507mtgabs

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DOI： 10.1149/MA2020-01432489mtgabs

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DOI： 10.1149/MA2018-01/34/2029

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DOI： 10.1149/MA2017-01/36/1700

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DOI： 10.1149/MA2016-01/32/1617

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DOI： 10.1149/MA2016-01/32/1590

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DOI： 10.1002/chin.200212082

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DOI： 10.1002/chin.200239250

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DOI： 10.1002/chin.201004086

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DOI： 10.1002/chin.200814085

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DOI： 10.1002/chin.200801025

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DOI： 10.1002/chin.200725042

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DOI： 10.1002/chin.200702104

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DOI： 10.1002/chin.200644198

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DOI： 10.1002/chin.200615043

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DOI： 10.1002/chin.200609212

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DOI： 10.1002/chin.200302068

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Event date： 2018.3.20 - 2018.3.23

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2017.11.15 - 2017.11.17

Language：English   Presentation type：Poster presentation  

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Event date： 2017.11.11 - 2017.11.12

Language：Japanese   Presentation type：Oral presentation (invited, special)  

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Event date： 2017.9.10 - 2017.9.11

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2017.9.7 - 2017.9.9

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2017.6.25 - 2017.6.29

Language：English   Presentation type：Poster presentation  

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Event date： 2017.6.22 - 2017.6.23

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2017.6.22 - 2017.6.23

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2017.6.22 - 2017.6.23

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2017.6.8 - 2017.6.10

Language：English   Presentation type：Oral presentation (invited, special)  

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Event date： 2017.3.16 - 2017.3.19

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2017.3.16 - 2017.3.19

Language：Japanese   Presentation type：Oral presentation (invited, special)  

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Event date： 2017.3.16 - 2017.3.19

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2017.3.16 - 2017.3.19

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2016.11.5 - 2016.11.6

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2016.9.14 - 2016.9.16

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2016.9.1 - 2016.9.3

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2016.6.24 - 2016.6.25

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2016.6.24 - 2016.6.25

Language：Japanese   Presentation type：Oral presentation (invited, special)  

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Event date： 2016.5.29 - 2016.6.3

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2016.5.29 - 2016.6.3

Language：English   Presentation type：Oral presentation (general)  

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Event date： 2016.5.29 - 2016.6.3

Language：English   Presentation type：Oral presentation (general)  

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Event date： 2016.4.22 - 2016.4.24

Language：English   Presentation type：Poster presentation  

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Event date： 2016.4.22 - 2016.4.24

Language：English   Presentation type：Oral presentation (invited, special)  

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Event date： 2016.3.29 - 2016.3.31

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2016.3.24 - 2016.3.27

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2016.3.24 - 2016.3.27

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2016.3.24 - 2016.3.27

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2015.12.15 - 2015.12.20

Language：English   Presentation type：Poster presentation  

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Event date： 2015.12.15 - 2015.12.20

Language：English   Presentation type：Oral presentation (general)  

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Event date： 2015.12.15 - 2015.12.20

Language：English   Presentation type：Oral presentation (general)  

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Event date： 2015.12.15 - 2015.12.20

Language：English   Presentation type：Poster presentation  

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Event date： 2015.11.19 - 2015.11.21

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2015.11.14 - 2015.11.15

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2015.11.9 - 2015.11.13

Language：English   Presentation type：Poster presentation  

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Event date： 2015.11.9 - 2015.11.13

Language：English   Presentation type：Oral presentation (general)  

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Event date： 2015.9.24 - 2015.9.26

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2015.9.7 - 2015.9.9

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2015.9.7 - 2015.9.9

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2015.9.7 - 2015.9.9

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2015.6.28 - 2015.7.2

Language：English   Presentation type：Poster presentation  

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Event date： 2015.6.26

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2015.6.25 - 2015.6.26

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2015.6.25 - 2015.6.26

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2015.6.25 - 2015.6.26

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2015.3.26 - 2015.3.29

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2015.3.26 - 2015.3.29

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2015.3.26 - 2015.3.29

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2015.3.26 - 2015.3.29

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2015.3.15 - 2015.3.17

Language：Japanese   Presentation type：Oral presentation (general)  

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Event date： 2015.2.12 - 2015.2.13

Language：English   Presentation type：Oral presentation (general)  

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Event date： 2014.11.14 - 2014.11.15

Language：English   Presentation type：Poster presentation  

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Event date： 2014.11.14 - 2014.11.15

Language：English   Presentation type：Poster presentation  

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Event date： 2014.9.22 - 2014.9.24

Language：English   Presentation type：Oral presentation (general)  

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Event date： 2014.9.7 - 2014.9.9

Language：Japanese   Presentation type：Poster presentation  

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Event date： 2014.7.13 - 2014.7.18

Language：English   Presentation type：Poster presentation  

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Event date： 2014.6.26 - 2014.6.27