Metal-free direct 1,6- and 1,2-difunctionalization triggered by radical trifluoromethylation of alkenes

Organic Letters
Lin HuangXin-Yuan Liu

Abstract

A metal-free direct remote C-H functionalization triggered by radical trifluoromethylation of alkenes was explored, realizing highly selective 1,6-difunctionalization of alkenes toward valuable trifluoromethyl α-hydroxycarbonyl compounds. Furthermore, a metal-free direct intermolecular regioselective 1,2-oxytrifluoromethylation of alkenes is also disclosed. With Togni's reagent as both the CF3 source and oxidant, the reaction exhibits a broad substrate scope with excellent functionality tolerance under mild metal-free conditions, thus showing great potential for synthetic utility.

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Feb 11, 2016·Chemical Reviews·Akira Yoshimura, Viktor V Zhdankin
Sep 15, 2016·The Journal of Organic Chemistry·Tian-Shu ZhangBo Jiang
Apr 26, 2017·Organic Letters·Xinkan YangGavin Chit Tsui
May 3, 2019·Organic & Biomolecular Chemistry·Hanyang BaoYunkui Liu
Sep 12, 2018·Beilstein Journal of Organic Chemistry·Igor B KrylovAlexander O Terent'ev
Jun 2, 2020·Chemical & Pharmaceutical Bulletin·Hiromichi Egami

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