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Regiospecific and Enantioselective Arylvinylcarbene Insertion of a C-H Bond of Aniline Derivatives Enabled by a Rh(I)-Diene Catalyst

文献类型：期刊论文

作者Zhu, Dong-Xing2; Xia, Hui1,3; Liu, Jian-Guo1,3; Chung, Lung Wa1,3; Xu, Ming-Hua1,2,3
刊名JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
出版日期2021-02-17
卷号143期号:6页码:2608-2619
ISSN号0002-7863
DOI10.1021/jacs.0c13191
通讯作者Chung, Lung Wa(oscarchung@sustech.edu.cn) ; Xu, Ming-Hua(xumh@sustech.edu.cn)
英文摘要Asymmetric insertion of an arylvinylcarbenoid into the C-H bond for direct enantioselective C(sp(2))-H functionalization of aniline derivatives catalyzed by a rhodium(I)-diene complex was developed for the first time. The reaction occurred exclusively at the uncommon vinyl terminus site with excellent E selectivity and enantioselectivities, providing various chiral gamma,gamma-gem-diarylsubstituted alpha,beta-unsaturated esters with broad functional group compatibility under simple and mild conditions. It provides a rare example of the asymmetric C-H insertion of arenes with selective vinylogous reactivity. Synthesis applications of this protocol were featured by several versatile product transformations. Systematic DFT calculations were also performed to elucidate the reaction mechanism and origin of the uncommon enantio- and regioselectivity of the Rh(I)-catalyzed C(sp(2))-H functionalization reaction. The measured and computed inverse deuterium kinetic isotope effect supports the C-C bond-formation step as the rate-determining step. Attractive interactions between the chiral ligand and substrates were also proposed to control the enantioselectivity.
资助项目National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002-006] ; National Natural Science Foundation of China[21672229] ; National Natural Science Foundation of China[21971103] ; National Natural Science Foundation of China[81521005] ; National Natural Science Foundation of China[21933003] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000621058200018
出版者AMER CHEMICAL SOC
源URL[http://119.78.100.183/handle/2S10ELR8/295724]  
专题新药研究国家重点实验室
通讯作者Chung, Lung Wa; Xu, Ming-Hua
作者单位1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
3.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China
推荐引用方式
GB/T 7714		 Zhu, Dong-Xing,Xia, Hui,Liu, Jian-Guo,et al. Regiospecific and Enantioselective Arylvinylcarbene Insertion of a C-H Bond of Aniline Derivatives Enabled by a Rh(I)-Diene Catalyst[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2021,143(6):2608-2619.
APA Zhu, Dong-Xing,Xia, Hui,Liu, Jian-Guo,Chung, Lung Wa,&Xu, Ming-Hua.(2021).Regiospecific and Enantioselective Arylvinylcarbene Insertion of a C-H Bond of Aniline Derivatives Enabled by a Rh(I)-Diene Catalyst.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,143(6),2608-2619.
MLA Zhu, Dong-Xing,et al."Regiospecific and Enantioselective Arylvinylcarbene Insertion of a C-H Bond of Aniline Derivatives Enabled by a Rh(I)-Diene Catalyst".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 143.6(2021):2608-2619.

入库方式： OAI收割

来源：上海药物研究所

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