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

A unique method for the synthesis of substituted 1-naphthols by a rhodium(ii)-catalysed ring-expansion reaction of 2-triazolyl-1-indanone derivatives is reported. 1,2-Acyl migration occurs with an intermediate alpha-imino rhodium carbenoid generated from the triazolyl moiety.

DOI： 10.1039/d1cc06349a

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

We report a new method for constructing propionate-derived trisubstituted alkene motifs in a stereoselective manner. 1-Substituted 1,1-di(pinacolatoboryl)-(E)-alk-2-enes are generated in situ from 1-substituted 1,1-di(pinacolatoboryl)alk-3-enes through ruthenium(II)-catalyzed double-bond transposition. These species undergo a chiral phosphoric acid catalyzed allylation reaction of aldehydes to produce the E isomers of anti-homoallylic alcohols. On the other hand, the corresponding Z isomers of anti-homoallylic alcohols are obtained when a dimeric palladium(I) complex is employed as the catalyst for this double-bond transposition. Thus, both E and Z isomers can be synthesized from the same starting materials. A B-C(sp(2)) bond remaining with the allylation product undergoes the Suzuki-Miyaura cross-coupling reaction to furnish a propionate-derived trisubstituted alkene motif in a stereo-defined form. The present method to construct the motifs with (E)- and (Z)-alkenes are successfully applied to the syntheses of (+)-isotrichostatic acid, (-)-isotrichostatin RK, and (+)-trichostatic acid, respectively.

DOI： 10.1002/chem.202004930

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

A synthesis of 3,5-disubstituted-1,2,4-triazoles from nitriles and 5-aryltetrazoles is reported. When 5-aryltetrazoles are triflylated in the presence of nitriles, the resulting 5-aryl-2-triflyltetrazoles thermally generate N-triflyl-nitrile imines through a sequence of ring-chain tautomerization and denitrogenation. The N-triflyl-nitrile imines immediately undergo 1,3dipolar cycloaddition with nitriles in a regioselective manner, forming the corresponding 1,2,4-triazoles.

DOI： 10.1246/cl.200634

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

A new synthetic method for alkyl sulfones through C-C bond formation between alkenes and tosylmethylphosphonium iodide is reported. A tosylmethyl radical is generated from the phosphonium iodide under irradiation of visible light with the aid of fac-Ir(ppy)(3). It undergoes regioselective 1,2-addition across the carbon-carbon double bond to afford an elongated alkyl radical, which abstracts a hydrogen atom from C6F5SH, producing an alkyl sulfone with one-carbon extension.

DOI： 10.1246/cl.200530

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

An chiral Rh-II-catalyzed cyclooligomerization reaction of thiophenes having triazolyl and vinyl substituents at the 2- and 4-positions was studied. Structurally interesting cyclic trimers, having chirality that is ascribed only to the orientation of the 2,4-disubstituted thiophene rings, are obtained. The 2,4-disubstitution of the starting thiophene monomer allows production of each of the enantiomers. The observed electronic circular-dichroism spectra are in accord with those simulated by density-functional theory calculations.

DOI： 10.1002/anie.202009781

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

Herein, we report a Rh(II)-catalyzed reaction between 1-tosyl-1,2,3-triazoles and halohydrins to provide 2,6-substituted 3,4-dihydro-2H-1,4-oxazines under basic conditions. The reaction is proposed to undergo a rhodium carbenoid 1,3-insertion into O-H followed by an annulation. The scope includes phenyl or alkenyl C4-substituted triazoles and a range of halohydrins using catalytic Rh(2)Oct(4) and K2CO3. A synthesis of the antimicrobial natural product (+/-)-chelonin C is also reported using this novel methodology.

DOI： 10.1021/acs.orglett.0c00947

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

We report the highly diastereo- and enantioselective preparation of (E)-delta-boryl-substituted anti-homoallylic alcohols in two steps from terminal alkynes. This method consists of a cobalt(II)-catalyzed 1,1-diboration reaction of terminal alkynes with B(2)pin(2) and a palladium(I)-mediated asymmetric allylation reaction of the resulting 1,1-di(boryl)alk-1-enes with aldehydes in the presence of a chiral phosphoric acid. Propyne, which is produced as the byproduct during petroleum refining, could be used as the starting material to construct homoallylic alcohols that are otherwise difficult to synthesize with high stereocontrol.

DOI： 10.1002/anie.201908299

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

A synthesis of chiral hydrocarbons having C-1 axis and C-3 symmetry, which owe their chirality due to asymmetrical distribution of C-12/C-13 isotopes, is reported. Their absolute configurations assigned using the vibrational circular dichroism technique conform with those deduced from the absolute configurations of the parent alpha-formyl cyclopropanes.

DOI： 10.1021/jacs.9b07181

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

An aldol-type reaction of boron aza-enolates with aldehydes is reported. N-Sulfonyl-1,2,3-triazoles react with pinacolborane in the presence of a nickel(0) catalyst to generate boron azaenolates with E geometry. The boron aza-enolates undergo an aldol-type reaction with aldehydes to give beta-boroxy imines with syn configuration. The subsequent one-pot reduction with DIBALH gives 1,3-amino alcohols.

DOI： 10.1246/cl.190290

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

A rhodium-catalyzed cyclization reaction of 4-acyl-1-sulfonyl-1,2,3-triazoles possessing a phenyl ring is reported. Generated acceptor/ acceptor carbenoids undergo cyclization by reacting either with a phenyl ring through electrophilic aromatic substitution or with a benzylic C-H bond through insertion depending on the length of the carbon chain.

DOI： 10.1246/cl.190074

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

An efficient method has been developed for the 1,2-hydro(cyanomethylation) of alkenes, in which a cyanomethyl radical species is generated from a cyanomethylphosphonium ylide by irradiation with visible light in the presence of an iridium complex, a thiol, and ascorbic acid. The cyanomethyl radical species then adds across the C=C double bond of an alkene to form an elongated alkyl radical species that accepts a hydrogen atom from the thiol to produce an elongated aliphatic nitrile. The ascorbic acid acts as the reductant to complete the catalytic cycle.

DOI： 10.1055/s-0037-1612230

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

The stereoselective synthesis of anti isomers of gamma-boryl-substituted homoallylic alcohols is disclosed. (E)-1,2-Di(boryl)alk-1-enes undergo Ru-catalyzed double-bond transposition with control of the geometry. The in situ generated (E)-1,2-di(boryl)alk-2-enes add to aldehydes in a stereospecific manner. The alkenylboron group within the product is amenable to a variety of synthetic derivatizations.

DOI： 10.1002/anie.201811205

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

Lignin model compounds undergo aerobic oxidation upon relay action of light and copper to afford isolable fragments. Considerably better efficiency and different product distribution are achieved in comparison to thermal copper-catalyzed aerobic fragmentation.

DOI： 10.1002/ajoc.201800520

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

A convenient method for synthesizing elongated aliphatic esters from alkenes is reported. An (alkoxycarbonyl)methyl radical species is generated upon visible-light irradiation of an ester-stabilized phosphorus ylide in the presence of a photoredox catalyst. This radical species adds onto the carbon-carbon double bond of an alkene to produce an elongated aliphatic ester.

DOI： 10.1002/anie.201809115

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

DOI： 10.1002/ange.201801283

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

Sulfonylation of 1H-tetrazoles with triflic anhydride in the presence of chiral rhodium(II) carboxylate dimers causes denitrogenation to generate -azo rhodium(II) carbenoid species as new types of donor/acceptor carbenoids, which then readily react with styrenes to afford 3,5-diaryl-2-pyrazolines with a high degree of enantioselectivity.

DOI： 10.1002/anie.201801283

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

A photocatalyzed reaction of pyridine N-oxides with alkenes gives ortho-alkylated pyridines with cleavage of the carbon-carbon double bond. Benzyl and secondary alkyl groups are incorporated at the ortho position of pyridines in one pot.

DOI： 10.1002/anie.201801305

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

A rhodium(II)-catalyzed reaction of newly prepared 4-acyl-1-sulfonyl-1,2,3-triazoles with benzene, and its derivatives, is investigated. Acceptor/acceptor carbenoids generated from 4-acyltriazoles undergo selective insertion at aromatic C(sp(2))-H bonds in the presence of benzylic C(sp(3))-H bonds to produce N-sulfonylenaminones.

DOI： 10.1002/anie.201709384

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

A cationic ruthenium(II) complex catalyzes double-bond transposition of 1,1-di(boryl)alk-3-enes to generate in situ 1,1-di(boryl)alk-2-enes, which then undergo chiral phosphoric acid catalyzed allylation of aldehydes producing homoallylic alcohols with a (Z)-vinylboronate moiety. 1,2-Anti stereochemistry is installed in an enantioselective manner. The (Z)-geometry forged in the products allows their isolation in a form of 1,2-oxaborinan-3-enes, upon which further synthetic transformations are operated.

DOI： 10.1021/jacs.7b06408

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

(E)-delta-Boryl-substituted anti-homoallylic alcohols are synthesized in a highly diastereo- and enantioselective manner from 1,1-di(boryl) alk-3-enes and aldehydes. Mechanistically, the reaction consists of 1) palladium-catalyzed double-bond transposition of the 1,1-di(boryl) alk-3-enes to 1,1-di(boryl) alk-2-enes, 2) chiral phosphoric acid catalyzed allylation of aldehydes, and 3) palladium-catalyzed geometrical isomerization from the Z to Eisomer. As a result, the configurations of two chiral centers and one double bond are all controlled with high selectivity in a single reaction vessel.

DOI： 10.1002/anie.201702611

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

An asymmetric synthesis of C-3-symmetric triangular macrocycles is reported. 1-Methylsulfonyl-4-(4-vinylphenyl)-1,2,3-triazole undergoes a rhodium(II)-catalyzed cyclotrimerization to establish an enantiopure C-3-symmetric triangular macrocycle motif. This method can be applied to the synthesis of an enantiopure hydrocarbon, which owes its chirality to asymmetric distribution of H/D atoms on the benzene rings.

DOI： 10.1002/anie.201612585

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

A study on a rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with 2-alkenols is reported. The reaction is initiated by insertion of an -imino carbene into the O-H linkage of alcohol, forming a 2-alkenoxy enamide intermediate. A thermal [3,3]-sigmatropic rearrangement follows to yield 2-substituted 2-amino ketone in a stereoselective manner. The successful application of this methodology to a formal synthesis of (-)--conhydrine is also described.

DOI： 10.1002/hlca.201600320

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

A rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with 2-(siloxy)furans is reported. Either open-chain penta-2,4-dien-1-imines or cyclic 1,2-dihydropyridines are selectively obtained depending on the ligand on rhodium(II).

DOI： 10.1021/acs.orglett.6b03143

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

Herein, the rhodium(II)-catalyzed cyclopropanation reaction of pinacol allylboronate with N-sulfonyl-1,2,3-triazoles is reported. Boryl-substituted cyclopropylmethanamines are produced in a highly diastereo- and enantioselective manner. Various cyclopropylmethanamines containing a quaternary stereocenter are derived from them.

DOI： 10.1246/cl.160465

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

A syn-selective aza-aldol reaction of boron aza-enolates, generated from N-sulfonyl-1,2,3-triazoles and 9-BBN-H, is reported. It provides a sequential one-pot procedure for the stereoselective construction of 1,3-amino alcohols, having contiguous stereocenters, starting from terminal alkynes.

DOI： 10.1002/anie.201603270

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

Aliphatic terminal alkenes react with pinacolborane at ambient temperature to afford dehydrogenative borylation compounds as the major product when iPr-Foxap is used as the ligand with cationic rhodium(I) in the presence of norbornene, which acts as the sacrificial hydrogen acceptor. The reaction is applied to the one-pot syntheses of aldehydes and homoallylic alcohols from aliphatic terminal alkenes.

DOI： 10.1002/anie.201506328

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

N-Sulfonyl-1,2,3-triazoles react with thioesters in the presence of a rhodium(II) catalyst to produce beta-sulfanyl enamides in a stereoselective manner. The reaction proceeds through generation of an a-imino rhodium carbene complex, nucleophilic addition of the sulfur atom of a thioester onto the carbenoid carbon atom, and subsequent intramolecular migration of the acyl group from the sulfur atom to the imino nitrogen atom. The method is successfully applied to a ring-expansion reaction of thiolactones, thus leading to the formation of sulfur-containing lactams.

DOI： 10.1002/anie.201504013

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

An enamido group is introduced site-selectively at the C(3)-position of indoles by the rhodium(II)-catalyzed reaction with N-sulfonyl-1,2,3-triazoles. Formally, an alpha-imino rhodium carbene complex is inserted into the C(3)-H bond of an indole.

DOI： 10.3987/COM-15-13261

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

A thermal reaction of 4-(p-aminophenyl)-1-sulfonyl-1,2,3-triazoles forming benzoyl cyanides is reported. A carbene species thermally generated from the triazole by denitrogenation undergoes intramolecular oxygen migration from sulfur to carbon, giving an N-sulfinyl benzoylimine intermediate. The subsequent Cope-type elimination of the sulfinyl group gives rise to cyano functionality.

DOI： 10.1246/cl.150320

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alpha,beta,gamma,delta-Unsaturated imines are synthesized from N-sulfonyl-1,2,3-triazoles and allenes. Allenes are initially cyclopropanated by intermediate alpha-imino rhodium carbene complexes, and the resulting allcylidenecyclopropyl methanimines undergo a ringopening thermal rearrangement to afford the corresponding alpha,beta,gamma,delta-unsaturated mimes.

DOI： 10.1246/cl.150080

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

A sequential procedure for the synthesis of 2,5-disubstituted thiazoles from terminal alkynes, sulfonyl azides, and thionoesters is reported. A copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with thionoesters in the presence of a rhodium(II) catalyst The resulting 3-sulfonyl-4-thiazolines subsequently aromatize into the corresponding 2,5-disubstituted thiazoles by elimination of the sulfonyl group.

DOI： 10.1021/acs.orglett.5b00960

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

Relay actions of copper, rhodium, and gold formulate a one-pot multistep pathway, which directly gives 2,5-dihydropyrroles starting from terminal alkynes, sulfonyl azides, and propargylic alcohols. Initially, copper-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with propargylic alcohols under the catalysis of rhodium. The resulting alkenyl propargyl ethers subsequently undergo the thermal Claisen rearrangement to give -allenyl--amino ketones. Finally, a gold catalyst prompts 5-endo cyclization to produce 2,5-dihydropyrroles.

DOI： 10.1002/chem.201405357

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An efficient one-pot two-step procedure for asymmetric synthesis of piperidine-fused trans-cycloalkenes is reported. The method comprises the initial enantioselective installation of another cyclopropane ring onto methylenecyclopropanes and the subsequent thermal skeletal rearrangement in which the installed and inherent cyclopropane rings are both opened. A concerted mechanism is proposed for the latter thermal rearrangement reaction together with a closed transition state model.

DOI： 10.1021/ja5096045

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

A rhodium-catalyzed reaction of formamides with N-sulfonyl-1,2,3-triazoles is developed to formulate a new one-pot procedure for the direct synthesis of a-amino enaminones from terminal alkynes.

DOI： 10.1021/ol5010774

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

A cationic rhodium(I) catalyst turns 2-silyl-1-alkenylboronate, readily prepared from a terminal alkyne, into the corresponding allylboronate species, which immediately undergoes nucleophilic addition to an aldehyde to give a syn-homoallylic alcohol stereoselectively.

DOI： 10.1021/ja502169d

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The rhodium-catalyzed dearomatizing [3 + 2] annulation reaction of 4-(3-arylpropyl)-1,2,3-triazoles is described. It provides a straightforward synthetic pathway from simple 5-aryl-1-alkynes leading to tricyclic 3,4-fused dihydroindoles via the corresponding 1,2,3-triazoles.

DOI： 10.1021/ja412663a

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

A new procedure for the stereoselective synthesis of syn alpha-amino beta-oxy ketones is reported. It consists of two steps; in the first step, alpha-amino silyl enol ethers having a (Z) geometry are prepared from 1-alkynes via 1-sulfonyl-1,2,3-triazoles. In the second step, the silyl enol ethers undergo the TiCl4-mediated Mukaiyama aldol reaction with aldehydes to produce alpha-amino beta-oxy ketones with excellent syn-selectivity.

DOI： 10.1039/c4cc04786a

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

1-Sulfonyl-1,2,3-triazoles undergo a Doyle-Kirmse reaction upon treatment with allylic sulfides in the presence of a rhodium(II) catalyst to afford alpha-allyl-alpha-sulfanylimines. Terminal alkynes are regioselectively multifunctionalized by the introduction of C-N, C-S, and C-C bonds through a one-pot sequence consisting of a [3 + 2] dipolar cycloaddition reaction with azide and subsequent Doyle-Kirmse reaction.

DOI： 10.1246/cl.130521

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DOI： 10.1021/ja407166r

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

We report a highly diastereo- and enantioselective synthesis of anti homoallylic alcohols from terminal alkynes via (E)-1-alkenylboronates based upon two catalytic reactions: a cationic iridium complex-catalyzed olefin transposition of (E)-1-alkenylboronates and a chiral phosphoric acid-catalyzed allylation reaction of aldehydes.

DOI： 10.1021/ja405790t

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DOI： 10.1021/ol401340u

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Two molecules of an isocyanate react with one molecule of a 1,3-diene in the presence of a nickel(0) catalyst to give a 6-substituted dihydropyrimidine-2,4-dione. A five-membered azanickelacyclic intermediate is initially generated through oxidative cyclization of a hetero-pair of the isocyanate and the 1,3-diene onto nickel(0). Another molecule of the isocyanate is subsequently incorporated therein and reductive elimination follows.

DOI： 10.1246/cl.130082

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DOI： 10.1002/anie.201209603

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DOI： 10.1021/ol302331k

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Enaminones are synthesized by the rhodium(II)-catalyzed denitrogenative rearrangement reaction of 1-(N-sulfonyl-1,2,3-triazol-4-yl)alkanols, which are readily prepared from propargylic alcohols and N-sulfonyl azides. Intramolecular 1,2-hydride (or -alkyl) migration occurs with an intermediary alpha-imino rhodium-(II) carbenoid species generated through denitrogenation of the 1,2,3-triazol-4-yl moiety. The resulting enaminones is converted into various heterocycles with replacement of the N-sulfonyl group.

DOI： 10.1021/ja308285r

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A copper(I)/2,2'-bipyridyl complex catalyzes an amination reaction of silyl ketene acetals with N-chloroamines, presenting a new preparative method of alpha-amino esters.

DOI： 10.1021/ol302331k

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2-Iodobenzamides reacted with alkynes in the presence of a nickel(0)/P(4-ClC6H4)(3) catalyst to produce substituted (1H)-isochromen-1-imines. The reaction proceeded through the formation of an oxanickelacycle, alkyne insertion, and reductive elimination.

DOI： 10.1246/cl.2012.798

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N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce alpha-amino ketones in high yield. An intermediary alpha-imino rhodium(II) carbenoid undergoes insertion into the O-H bond of water. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.

DOI： 10.1021/ja2104203

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DOI： 10.1002/anie.201105148

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One molecule of acrylate reacts with two molecules of isocyanate in the presence of a nickel(0)/SIPr catalyst to give a 1,3,5-trisubstituted hydantoin. Two processes operate in sequence, the first, regioselective formation of N-substituted fumaramate from acrylate and isocyanate and, the second, ring closure of the fumaramate with incorporation of another molecule of isocyanate.

DOI： 10.1021/ol200957y

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A rhodium(I)/dppe catalyst promoted dimerization of monosubstituted allenes in a stereoselective manner to give cross-conjugated trienes, which are different from those obtained by a palladium catalyst.

DOI： 10.3762/bjoc.7.67

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1,2,3-Benzotriazin-4(3H)-ones and 1,2,3,4-benzothiatriazine 1,1(2H)-dioxide reacted with isocyanides in the presence of a palladium catalyst to give 3-(imino)isoindolin-1-ones and 3-(Imino)thiaisoindoline 1,1-dioxides, respectively, In high yield. An intermediate azapalladacycie was generated through denitrogenation of the triazine moiety, and an isocyanide was Incorporated therein.

DOI： 10.1021/ol103143a

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DOI： 10.1002/anie.201105077

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DOI： 10.1021/ja105541r

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A palladium-catalyzed cyclization reaction of 2-(alkynyl)-aryl isocyanates with copper(I) cyanide provides an efficient method for the stereoselective synthesis of (Z)-configured 3-(1-cyanoalkyhdene)oxindoles

DOI： 10.1246/cl.2010.1132

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Alkynyl(aryl)(diorganyl)borates, anionic tetrahedral boron compounds, reacted with allylic bromides in the presence of a palladium(0) catalyst to produce (diorganyl)(trisubstituted alkenyl)boranes. Allylation took place at the allcynyl carbon beta to boron, inducing 1,2-migration of the aryl group on the anionic boron center to the alpha-carbon.

DOI： 10.1246/bcsj.20100189

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A palladium complex sequentially promoted two mechanistically distinct reactions, the first, cyclization of 2-(alkynyl)aryl isocyanates with benzylic alcohols, and the second, [1,3] rearrangement of a benzyl group from oxygen to carbon, furnishing 3,3-disubstituted oxindoles in one pot

DOI： 10.1021/ol101892b

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

1,2,3-Benzotriazin-4(3H)-ones react with 1,3-dienes in the presence of a nickel(0)/phosphine complex to give a variety of 3,4-dihydroisoquinolin-1(2H)-ones. Oxidative insertion of nickel(0) into the triazinone moiety prompts extrusion of dinitrogen to give a five-membered ring azanickelacyclic intermediate. Subsequent insertion of 1,3-dienes into the nickel-carbon bond followed by allylic amidation affords 3,4-dihydroisoquinolin-1(2H)-ones. Alkenes also undergo insertion into the five-membered ring azanickelacyclic intermediate, and subsequent reductive elimination gives 3-substituted 3,4-dihydroisoquinolin-1(2H)-ones.

DOI： 10.1021/jo1008756

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

1,2-Rearrangement of a sulfonyl group occurs on treatment of 1-sulfony1-1,2,3-triazoles with a catalytic amount of 4-dimethylaminopyridine (DMAP) in acetonitrile to give an equilibrium mixture of 1-sulfonyl- and 2-sulfonyl derivatives, with considerable predominance of the latter. Subsequent acidic treatment of the mixture caused selective hydrolysis of the 1-sulfonyl derivative, which led to the isolation of the 2-sulfony1-1,2,3-triazole in good total yield in a pure form.

DOI： 10.3987/COM-09-S(S)44

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

A denitrogenative annulation reaction of 1,2,3-benzotriazin-4(3H)-ones with allenes catalyzed by a nickel-phosphine complex to produce a variety of substituted 3,4-dihydroisoquinolin-1(2H)-ones in a regioselective manner is described. A highly enantioselective version, as well as structural evidence for the mechanistic course of this reaction, is also presented.

DOI： 10.1021/ja909603j

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Language：English  

DOI： 10.1002/anie.201001918

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

Vinyl-substituted (Z)-stilbenes are stereoselectively synthesised on treatment of 4-arylbuta-2,3-dien-1-ols with arylboronic acids in the presence of a rhodium(I) catalyst. The reaction proceeds through the regioselective addition of organorhodium(I) species across the aryl-substituted carbon-carbon double bond of the allene moiety and subsequent delta-elimination of Rh(I)-OH.

DOI： 10.1039/c0ob00163e

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：WILEY-BLACKWELL  

DOI： 10.1002/anie.201001918

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

The palladium-catalyzed reactions of 2-(alkynyl)aryl iso-cyanates with thiols and alcohols caused cyclization to give stereodefined 3-alkylideneoxindoles incorporating sulfanyl and alkoxy groups on the alkylidene unit, respectively.

DOI： 10.1246/cl.2009.1174

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A rhodium-catalyzed reaction of alkynyl oxiranes with arylboronic acids affords syn-configured alpha-allenols with high diastereoselectivity. The reaction is initiated by addition of an arylrhodium(I) specie; onto the alkyne moiety of the alkynyl oxirane. The resulting alkenylrhodium(I) intermediate undergoes beta-oxygen elimination to open the oxirane ring in a syn-selective fashion. Protonolysis of the rhodium(I) alkoxide with arylboronic acid releases the corresponding alpha-allenol along with the rhodium(I) boronate, Which undergoes beta-aryl elimination to regenerate the arylrhodium(I) species. The utility of this method is demonstrated by an application to a concise synthesis of (+/-)-Boivinianin B.

DOI： 10.1021/jo900987w

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

A new cyclization reaction occurred on treatment of 2-(alkynyl)aryl isocyanates with amides in the presence of a palladium(0)/diphosphine catalyst to stereoselectively form 3-(amidoalkylidene)oxindoles. A carbon-nitrogen bond as well as a carbon-carbon bond were simultaneously introduced onto the alkyne moiety to construct an oxindole skeleton with stereoselective placement of the amino substituent cis to the carbonyl group.

DOI： 10.1021/ol900759f

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

Treatment of N-tosylphenylacetamide derivatives with copper(II) acetate in the presence of a catalytic amount of palladium(II) acetate affords 3,3-disubstituted oxindoles. The reaction proceeds through the intramolecular metallation of an aromatic C-H bond and the following C-N bond formation by reductive elimination.

DOI： 10.1246/cl.2009.328

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N-Sulfonyl-1,2,3-triazoles reacted with alkynes in the presence of a nickel(0)/phosphine catalyst to give substituted pyrroles, with the extrusion of molecular nitrogen; the triazole moiety isomerised to an alpha-imino diazo species, and the denitrogenative addition to nickel(0) was followed by the insertion of alkynes and reductive elimination.

DOI： 10.1039/b819162j

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

A palladium(0)/monophosphine catalyst promotes a cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents to produce stereodefined 3-alkylideneoxindoles. The alkynyl and isocyanato groups undergo oxidative cyclization with Pd(0) to form an oxapalladacycle intermediate. Subsequent transmetalation and reductive elimination afford the product.

DOI： 10.1021/ol801844w

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

Treatment of alpha-(trifluoromethyl)styrenes with arylboronic esters and MeMgCl in the presence of a rhodium(I) catalyst affords gem-difluoroalkenes. The reaction proceeds through the addition of arylrhodium(I) species across the electron-deficient carbon-carbon double bond and the subsequent beta-floride elimination.

DOI： 10.1246/cl.2008.1006

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

1,2,3-Benzotriazin-4(3(H)-ones reacted with internal and terminal alkynes in the presence of a nickel(0)/phosphine catalyst to give a wide range of substituted 1(2H)-isoquinolones in high yield. The reaction proceeded through denitrogenative activation of the triazinone moiety and the following insertion of alkynes.

DOI： 10.1021/ol8010826

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

2-Alkynylaryl isocyanates reacted with bis(pinacolato)diboron in the presence of a cationic rhodium(I) catalyst to produce borylated 3-alkylideneoxindoles stereoselectively. The carbon-boron linkage formed was further transformed via reactions such as a cross-coupling and a halogenation reaction.

DOI： 10.1021/ol800380t

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

Methoxy-substituted 1,6-enynes react with arylboronic acids in the presence of a rhodium(I) complex to give arylated cyclization products. This occurs by a multi-step mechanism consisting of rhodium/boron transmetalation, intermolecular carborhodation, intramolecular carborhodation, beta-hydride elimination, hydrorhodation, and beta-oxygen elimination. A shift of the position of a carbon-carbon double bond is observed, suggesting that the beta-hydride elimination/hydrorhodation process is repeatedly taking place.

DOI： 10.1002/asia.200700407

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

Allenynes having malonate-based tethers reacted with arylboronic acids in the presence of a rhodium(I) catalyst to sequentially form three carbon-carbon bonds, and arylated bicyclic skeletons were constructed in a stereoselective manner.

DOI： 10.1039/b810665g

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Language：English  

DOI： 10.1021/ol7024185

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

The addition reaction of aryl- and alkenylboronic acids to isocyanates is catalysed by a rhodium(i) complex, affording secondary amides under mild conditions.

DOI： 10.1039/b709203b

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

Divnes having malonate-based tethers react with aryl-boronic acids in the presence of a rhodium(l) catalyst to give 1,2dialkylidenecycloalkanes. The regioselectivity of the initial carborhodation depends on the sterics and the directing nature of the alkyne substituents.

DOI： 10.1055/s-2007-984879

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

Alkynones react with arylboronic acids in the presence of a rhodium(I) catalyst to afford four- and five-membered-ring cyclic alcohols equipped with a tetrasubstituted exocyclic olefin. The cyclic allylic alcohol skeleton is constructed by the carbon-carbon bond formation between the carbonyl group and an alkenylrhodium(I) intermediate formed by the regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond. (c) 2007 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tet.2007.03.025

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

A stoichiometric amount of nickel(0) complex mediated the aminative carboxylation of unsaturated hydrocarbons through oxidative cyclization with carbon dioxide followed by insertion of dibenzoyldiazene into the carbon-nickel bond, giving beta-amino acid derivatives.

DOI： 10.1246/cl.2007.476

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Unsaturated esters possessing a pendent cyano moiety react with B-Ar-9-BBNs in the presence of a rhodium(I) catalyst to give the five- and six-membered beta-enamino esters in good yield. An (oxa-pi-allyl)rhodium(I) intermediate, formed by initial conjugate addition of an Ar-rhodium(I) species, undergoes a facile intramolecular addition to the cyano group to construct the carbocyclic skeletons.

DOI： 10.1021/ol062882y

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER SCIENCE SA  

On treatment of 5-siloxy-1,2,5-trienes with a catalytic amount Of W(CO)(6) under photoirradiation, two types of synthetically useful compounds, that is, 6-endo-cyclized products or formal Cope rearrangement products, are obtained selectively via the same intermediates simply by changing reaction conditions. In these reactions, electrophilic activation of the allene moiety is effectively achieved by coordination Of W(CO)(5), allowing intramolecular attack by neutral carbon nucleophiles in a 6-endo manner. (c) 2006 Elsevier B.V. All rights reserved.

DOI： 10.1016/j.jorganchem.2006.08.037

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Substitutive arylation of cis-allylic diols occurs upon treatment with arylboroxines in the presence of a rhodium(I) catalyst; the reaction proceeds through the addition of an intermediate arylrhodium(I) species across the carbon-carbon double bond and subsequent beta-oxygen elimination.

DOI： 10.1039/b612710j

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

DOI： 10.1002/anie.200701505

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The palladium-catalysed reaction of alkynyltriarylborates with aryl halides afforded trisubstituted alkenylboranes, in which two different aryl groups were installed across the carbon carbon double bond in a cis arrangement.

DOI： 10.1039/b710472c

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

This article highlights recent developments in the formation of carbocycles via multiple carborhodation steps triggered by the rhodium-catalysed intermolecular addition of organoborons. Various types of cascade reactions have been developed to demonstrate that multiple carborhodation steps can precede potentially competing processes such as protonolysis.

DOI： 10.1039/b609991b

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

The reaction of arylboronic acids with 1,6-enynes that contain an allylic ether moiety is catalyzed by a rhodium(I) complex to produce cyclopentanes with a tetrasubstituted exo olefin and a pendant vinyl group. The reaction is initiated by the regioselective addition of an arylrhodium(l) species to the carbon-carbon triple bond of the 1,6-enyne. The resulting alkenylrhodium(I) compound subsequently undergoes intramolecular carborhodation of the allylic double bond in a 5exo-trig mode. beta Elimination of the methoxy group affords the cyclization product and the catalytically active methoxorhodium(I) species. The use of alkyl Grignard reagents instead of aryiboronic acids as organometallic nucleophiles was also examined.

DOI： 10.1002/asia.200600254

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DOI： 10.1021/ja0575326

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

DOI： 10.1002/anie.200602188

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

DOI： 10.1039/b515684j

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

DOI： 10.1002/anie.200502650

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DOI： 10.1021/ol051249u

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

DOI： 10.1021/ja0435079

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

DOI： 10.1021/ja043123i

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

DOI： 10.1055/s-2005-863718

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DOI： 10.1039/b511779h

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DOI： 10.1039/b503686k

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DOI： 10.1021/ol0473694

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

DOI： 10.1016/j.molcata.2003.10.050

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DOI： 10.1021/ja035988m

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DOI： 10.1021/ol034365a

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DOI： 10.1021/ol026993i

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DOI： 10.1021/ja0113091

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DOI： 10.1021/ol0068041

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DOI： 10.1021/jo991460h

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DOI： 10.1016/s0040-4039(99)00856-4

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Publisher：John Wiley & Sons, Ltd  

DOI： 10.1002/047084289x.rn00904

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Publisher：John Wiley & Sons, Ltd  

DOI： 10.1002/047084289x.rn00905

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