A Concise Copper-Catalyzed Oxytrifluoromethylation of Allyl Alcohols

In deep memory of Dr. Ei-ichi Negishi.

Abstract

An efficient oxytrifluoromethylation of 1-aryl-substituted allyl alcohols has been developed using Togni’s reagent II as a trifluoromethylation reagent and copper(I) chloride as a catalyst. This reaction proceeded through a one-pot process of trifluoromethylation followed by nucleophilic attack of the vicinal hydroxyl group. This strategy features good diastereoselectivity and broad substrate scope, which provides a facile access to various 2-aryl-3-(2,2,2-trifluoroethyl)oxiranes.

Key words

oxytrifluoromethylation - allyl alcohols - CF₃-substituted epoxides­ - Togni’s reagent - copper catalysis - 2-(2,2,2-trifluoroethyl)oxiranes­

Publication History

Received: 18 September 2021

Accepted after revision: 18 October 2021

Accepted Manuscript online:
18 October 2021

Article published online:
30 November 2021

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