南方科技大学知识苑(SUSTech KC): Rhodium(I)-Catalyzed Enantioselective C(sp(3))-H Functionalization via Carbene-Induced Asymmetric Intermolecular C-H Insertion(dagger)

题名	Rhodium(I)-Catalyzed Enantioselective C(sp(3))-H Functionalization via Carbene-Induced Asymmetric Intermolecular C-H Insertion(dagger)
作者	Liu, Bo1,2,3 ; Xu, Ming-Hua1,2
通讯作者	Xu, Ming-Hua
发表日期	2021-05-01
DOI	10.1002/cjoc.202100040
发表期刊	CHINESE JOURNAL OF CHEMISTRY 影响因子和分区
ISSN	1001-604X
EISSN	1614-7065
摘要	["Main observation and conclusion","Transition-metal-catalyzed C-H insertion of metal-carbene represents an excellent and powerful approach for C-H functionalization. However, despite remarkable advances in metal-carbene chemistry, transition metal catalysts that are capable of enantioselective intermolecular carbene C-H insertion are mainly constrained to dirhodium(II) and iridium(III)-based complexes. Herein, we disclose a new version of asymmetric carbene C-H insertion reaction with rhodium(I) catalyst. A highly enantioselective rhodium(I) complex-catalyzed C(sp(3))-H functionalization of 1,4-cyclohexadienes with alpha-aryl-alpha-diazoacetates was successfully developed. By using chiral bicyclo[2.2.2]-octadiene as ligand, rhodium(I)-carbene-induced asymmetric intermolecular C-H insertion proceeds smoothly at room temperature, allowing access to a diverse variety of alpha-aryl-alpha-cyclohexadienyl acetates and gem-diaryl-containing acetates in good yields with good to excellent enantioselectivities (up to 99% ee). Furthermore, the synthetic utility of the reaction was highlighted by facile synthesis of a novel cannabinoid CB1 receptor ligand. This method may offer a new opportunity for the development of therapeutically exploitable cannabinoid receptor type ligands in medicinal chemistry."]
关键词	Asymmetric catalysis C-H functionalization carbene C-H insertion Rhodium
相关链接	[来源记录]
收录类别	SCI
语种	英语
学校署名	第一 ; 通讯
资助项目	National Natural Science Foundation of China[21971103,21672229] ; National Science & Technology Major Project "Key New Drug Creation and Manufacturing Program", China[2018ZX09711002-006] ; Guangdong Provincial Key Laboratory of Catalysis["2020B121201002","(1R,4R)-5"]
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000655102200001
出版者	WILEY-V C H VERLAG GMBH
ESI学科分类	CHEMISTRY
来源库	Web of Science
引用统计	被引频次[WOS]：22
成果类型	期刊论文
条目标识符	http://sustech.caswiz.com/handle/2SGJ60CL/229426
专题	深圳格拉布斯研究院理学院_化学系
作者单位	1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, 1088 Xueyuan Blvd, Shenzhen 518055, Guangdong, Peoples R China 2.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, 1088 Xueyuan Blvd, Shenzhen 518055, Guangdong, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China
第一作者单位	深圳格拉布斯研究院; 化学系
通讯作者单位	深圳格拉布斯研究院; 化学系
第一作者的第一单位	深圳格拉布斯研究院
推荐引用方式 GB/T 7714	Liu, Bo,Xu, Ming-Hua. Rhodium(I)-Catalyzed Enantioselective C(sp(3))-H Functionalization via Carbene-Induced Asymmetric Intermolecular C-H Insertion(dagger)[J]. CHINESE JOURNAL OF CHEMISTRY,2021.
APA	Liu, Bo,&Xu, Ming-Hua.(2021).Rhodium(I)-Catalyzed Enantioselective C(sp(3))-H Functionalization via Carbene-Induced Asymmetric Intermolecular C-H Insertion(dagger).CHINESE JOURNAL OF CHEMISTRY.
MLA	Liu, Bo,et al."Rhodium(I)-Catalyzed Enantioselective C(sp(3))-H Functionalization via Carbene-Induced Asymmetric Intermolecular C-H Insertion(dagger)".CHINESE JOURNAL OF CHEMISTRY (2021).