Copper Catalyzed Enantioconvergent Nucleophilic Substitutions

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外文摘要：As a versatile earth-abundant transition metal,Cu has long been widely applied in the C-C and C-X bond forming reactions.As for now,low-valent Cu(Ⅰ)is known to reduce the redox active electrophiles via an SET pathway to give the corresponding radical and Cu(Ⅱ)species.The resulting Cu(Ⅱ)species can interact with the radical via the out-sphere pathway,affording the coupling product.Alternatively,Cu(Ⅱ)can trap the radical through the inner-sphere process to generate Cu(Ⅲ)species and then realize challenging bond formations due to the facile reductive elimination of Cu(Ⅲ)intermediate.Although copper catalysis has been widely applied in arylations of various nucleophiles,copper-catalyzed enantioconvergent nucleophilic substitutions of racemic alkyl electrophiles have been less explored,likely due to the difficulties in overcoming the reduction potential of alkyl electrophiles,elimination of side reac-tions,and enantiomeric control.In order to overcome the high reduction potential of alkyl electrophiles,the photo-induced strategy has been developed under mild conditions.An alternative strategy with new anionic tridentate ligands has also been reported in this regard.This review summarizes recent developments in copper-catalyzed enantioconvergent nucleophilic substitutions of alkyl elec-trophiles by various nucleophiles to realize C-N,C-C,C-B,C-P and C-O bond formations and their brief mechanistic studies.

外文关键词：

EnantioconvergentNucleophilic substitutionCopperRadical reactionsPhotocatalysisAsymmetric catalysis

作者：

Chunxi Huang、Zilong Wan、Aoping Zhu、Caiyou Chen

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作者单位：

College of Chemistry and Molecular Sciences,Wuhan University,Wuhan,Hubei 430072,China

Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules and College of Chemistry and Chemical Engineering,Hubei University,Wuhan,Hubei 430062,China

基金：

Key Research and Development Program of the Ministry of Science and Technology of Chinastartup funding from Wuhan University

项目编号：

2023YFA1508600

出版年：

2024

DOI：

10.1002/cjoc.202300622

中国化学(英文版)

中国化学会上海有机化学研究所

中国化学(英文版)

CSTPCD

影响因子：0.848

ISSN：1001-604X

年,卷(期)：2024.42(10)