Palladium-Catalyzed Remote C-H Phosphonylation of Indoles at the C4 and C6 Positions by a Radical Approach

doi:10.1002/anie.202103395

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	Palladium-Catalyzed Remote C-H Phosphonylation of Indoles at the C4 and C6 Positions by a Radical Approach
	Shi, Xiaolin 1,2,3; Wang, Zemin ; Li, Yuxiu ; Li, Xiaowei1 ; Li, Xiangqian 1; Shi, Dayong 1,4
	2021-05-11
发表期刊	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN	1433-7851
页码	7
通讯作者	Shi, Dayong(shidayong@sdu.edu.cn)
摘要	Palladium-catalyzed direct C-H activation of indole benzenoid moiety has been achieved in the past decade. However, palladium-catalyzed remote C-H activation of indoles is rare. Herein, we report a challenging palladium-catalyzed remote C4-H phosphonylation of indoles by a radical approach. The method provides access to a series of C4-phosphonylated indoles, including tryptophan and tryptophan-containing dipeptides, which are typically inaccessible by direct C4-H activation due to its heavy reliance on C3 directing groups. Notably, unexpected C6-phosphonylated indoles were obtained through blocking of the C4 position. The preliminary mechanistic studies indicated that the reactions may proceed via a C7-palladacycle/remote-activation process. Based on the strategy, examples of remote C4-H difluoromethylation with BrCF2COOEt are also presented, suggesting that the strategy may offer a general blueprint for other cross-couplings.
关键词	C− H activation indoles palladium phosphonylation regioselectivity
DOI	10.1002/anie.202103395
收录类别	SCI
语种	英语
资助项目	National Program for Support of Top-notch Young Professionals ; Fund of Taishan scholar project ; Shandong Provincial Natural Science Foundation for Distinguished Young Scholars[JQ201722] ; Qingdao Science and Technology Benefit People Demonstration Guide Special Project[20-3-4-20-nsh] ; Shandong University[2020GN033]
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:000649184600001
出版者	WILEY-V C H VERLAG GMBH
引用统计	被引频次：13[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.qdio.ac.cn/handle/337002/170616
专题	实验海洋生物学重点实验室
通讯作者	Shi, Dayong
作者单位	1.Shandong Univ, State Key Lab Microbial Technol, 72 Binhai Rd, Qingdao 266237, Shandong, Peoples R China 2.Chinese Acad Sci, Inst Oceanol, Key Lab Expt Marine Biol, Qingdao 266071, Peoples R China 3.Univ Chinese Acad Sci, Beijing 101408, Peoples R China 4.Pilot Natl Lab Marine Sci & Technol, Lab Marine Biol & Biotechnol, 168 Weihai Rd, Qingdao 266237, Shandong, Peoples R China
第一作者单位	实验海洋生物学重点实验室
推荐引用方式 GB/T 7714	Shi, Xiaolin,Wang, Zemin,Li, Yuxiu,et al. Palladium-Catalyzed Remote C-H Phosphonylation of Indoles at the C4 and C6 Positions by a Radical Approach[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2021:7.
APA	Shi, Xiaolin,Wang, Zemin,Li, Yuxiu,Li, Xiaowei,Li, Xiangqian,&Shi, Dayong.(2021).Palladium-Catalyzed Remote C-H Phosphonylation of Indoles at the C4 and C6 Positions by a Radical Approach.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,7.
MLA	Shi, Xiaolin,et al."Palladium-Catalyzed Remote C-H Phosphonylation of Indoles at the C4 and C6 Positions by a Radical Approach".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021):7.

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