Chemistry

Nucleophilic trifluoromethoxylation of alkyl halides without silver

Y. Li, Y. Yang, et al.

This groundbreaking research by Yan Li, Yang Yang, Jinrui Xin, and Pingping Tang introduces a novel nucleophilic trifluoromethoxylation method for alkyl halides using (E)-O-trifluoromethyl-benzaldoximes (TFBO) as a reagent. This approach offers a practical solution to preparing molecules with the trifluoromethoxy group, essential for pharmaceuticals and agrochemicals, under mild conditions and without silver, showcasing impressive functional group compatibility.... show more

Abstract

The biological properties of molecules containing the trifluoromethoxy group have made these compounds important targets in pharmaceuticals and agrochemicals, yet their preparation is still a substantial challenge. Herein, we present a practical nucleophilic trifluoromethoxylation of alkyl halides with (E)-O-trifluoromethyl-benzaldoximes (TFBO) as a trifluoromethoxylation reagent in the absence of silver under mild reaction conditions. The trifluoromethoxylation reagent TFBO is easily prepared and thermally stable, and can release CF₃O species in the presence of a base. Furthermore, broad scope and good functional group compatibility are demonstrated by application of the method to the late-stage trifluoromethoxylation of alkyl halides in complex small molecules.

Publisher

Nature Communications

Published On

Feb 06, 2020

Authors

Yan Li, Yang Yang, Jinrui Xin, Pingping Tang

DOI

https://doi.org/10.1038/s41467-020-14598-1

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