Electrochemical Trifluoromethylation of Glycals

J Org Chem. 2021 Nov 19;86(22):16187-16194. doi: 10.1021/acs.joc.1c01318. Epub 2021 Aug 26.

Abstract

Carbohydrates play essential roles in various physiological and pathological processes. Trifluoromethylated compounds have wide applications in the field of medicinal chemistry. Herein, we report a practical and efficient trifluoromethylation of glycals by an electrochemical approach using CF3SO2Na as the trifluoromethyl source and MnBr2 as the redox mediator. A variety of trifluoromethylated glycals bearing different protective groups are obtained in 60-90% yields with high regioselectivity. The successful capture of a CF3 radical indicates that a radical mechanism is involved in this reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Oxidation-Reduction*