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Nucleophilic trifluoromethoxylation of alkyl halides without silver.

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.

SUBMITTER: Li Y

PROVIDER: S-EPMC7005179 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Nucleophilic trifluoromethoxylation of alkyl halides without silver.

Li Yan Y Yang Yang Y Xin Jinrui J Tang Pingping P

Nature communications 20200206 1

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 a ...[more]

PMID: 32029731

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