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

文献类型：期刊论文

作者Shi, Xiaolin1,3,4; Wang, Zemin; Li, Yuxiu; Li, Xiaowei3; Li, Xiangqian3; Shi, Dayong2,3
刊名ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
出版日期2021-05-11
页码7
关键词C− H activation indoles palladium phosphonylation regioselectivity
ISSN号1433-7851
DOI10.1002/anie.202103395
通讯作者Shi, Dayong(shidayong@sdu.edu.cn)
英文摘要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.
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
语种英语
WOS记录号WOS:000649184600001
出版者WILEY-V C H VERLAG GMBH
源URL[http://ir.qdio.ac.cn/handle/337002/170615]  
专题海洋研究所_实验海洋生物学重点实验室
通讯作者Shi, Dayong
作者单位1.Univ Chinese Acad Sci, Beijing 101408, Peoples R China
2.Pilot Natl Lab Marine Sci & Technol, Lab Marine Biol & Biotechnol, 168 Weihai Rd, Qingdao 266237, Shandong, Peoples R China
3.Shandong Univ, State Key Lab Microbial Technol, 72 Binhai Rd, Qingdao 266237, Shandong, Peoples R China
4.Chinese Acad Sci, Inst Oceanol, Key Lab Expt Marine Biol, Qingdao 266071, Peoples R China
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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来源：海洋研究所

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