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Aqueous Benzylic C-H Trifluoromethylation for Late-Stage Functionalization.

ABSTRACT: The installation of trifluoromethyl groups has become an essential step across a number of industries such as agrochemicals, drug discovery, and materials. Consequently, the rapid introduction of this critical functional group in a predictable fashion would benefit current practitioners in those fields. This communication describes a mild trifluoromethylation of benzylic C-H bonds with high selectivity for the least hindered hydrogen atom. The reaction provides monotrifluoromethylation and proceeds in an environmentally friendly acetone/water solvent system. The method can be used to install benzylic trifluoromethyl groups on highly functionalized drug molecules.

SUBMITTER: Guo S

PROVIDER: S-EPMC6310231 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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Aqueous Benzylic C-H Trifluoromethylation for Late-Stage Functionalization.

Guo Shuo S AbuSalim Deyaa I DI Cook Silas P SP

Journal of the American Chemical Society 20180924 39

The installation of trifluoromethyl groups has become an essential step across a number of industries such as agrochemicals, drug discovery, and materials. Consequently, the rapid introduction of this critical functional group in a predictable fashion would benefit current practitioners in those fields. This communication describes a mild trifluoromethylation of benzylic C-H bonds with high selectivity for the least hindered hydrogen atom. The reaction provides monotrifluoromethylation and proce ...[more]

PMID: 30247886

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