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Updated: Jul 12, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Umpolung trifluoromethylthiolation of alcohols
Ye Yang1, Jiemin Ma1, Jiaxiang Zhang1
1School of Chemistry and Chemical Engineering, Nanchang University, Nanchang, Jiangxi 330031, China. caihu@ncu.edu.cn.
Abstract:
Herein we develop a metal-free umpolung dehydroxytrifluoromethylthiolation of alcohols with commercially available PPh3 and N-trifluoromethylthiophthalimide within 30 minutes. This protocol shows excellent functional group tolerance and high regioselectivity. The dehydroxytrifluoromethylthiolation of a series of natural products and drugs further demonstrates its practicality. Preliminary mechanistic studies suggest that PPh3 is responsible for deoxygenation and the key trifluoromethylthiophosphonium ion may be hydrolyzed by H2O in solvent.
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