Rh-Catalyzed C-H bond alkylation of indoles with α,α-difluorovinyl tosylate via indolyl group migration

Chemical Communications : Chem Comm
Lu ZhouChao Feng

Abstract

Herein we demonstrate that an alkylation of indoles could be accessed through C-H bond functionalization with α,α-difluorovinyl tosylate. The key aspect for the effective alkylation is the influence of the fluorine substituents on the reactivity of the C[double bond, length as m-dash]C double bond, allowing regioselective insertion as well as an indolyl group shift process. Furthermore, the fluorides are removed through alcoholysis to furnish the alkylation product as a traceless auxiliary.

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Citations

Jan 30, 2019·Angewandte Chemie·Haidong LiuChao Feng
Jun 12, 2020·Israel Journal of Chemistry·Suvajit Koley, Ryan A Altman
Apr 3, 2020·Chemical Communications : Chem Comm·Zhiqiang PanChengfeng Xia
Nov 8, 2018·The Journal of Organic Chemistry·Chuangchuang Xu, Jiaxi Xu
May 14, 2019·The Journal of Organic Chemistry·Lisheng YangHong Liu

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