Trifluoromethylation-initiated remote cross-coupling of carbonyl compounds to form carbon-heteroatom/carbon bonds

Chemistry : a European Journal
Lin HuangXin-Yuan Liu

Abstract

By involving the reversal of conventional reactivity expectations without external oxidants, we describe a novel and convenient protocol of remote cross-coupling of carbonyl compounds with a series of common and simple nucleophiles. This cross-coupling is triggered by radical trifluoromethylation of alkenes, thereby achieving highly selective remote difunctionalization of alkenes and α-position of the carbonyl group for facile access to trifluoromethyl α-halo- and α-cyanocarbonyl compounds. The reaction exhibits a broad substrate scope with excellent functionality tolerance and many different types of nucleophiles; further synthetic applicability of the obtained compounds proved to be suitable, thus showing great potential for synthetic utility.

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Citations

Jul 15, 2015·Organic & Biomolecular Chemistry·Sadhan JanaSangit Kumar
Jun 2, 2020·Chemical & Pharmaceutical Bulletin·Hiromichi Egami
Jan 13, 2017·Angewandte Chemie·Xingliang NieGangguo Zhu

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