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Efficient Synthesis of Trifluoromethyl Amines through a Formal Umpolung Strategy from the Bench-Stable Precursor (Me₄ N)SCF₃.

ABSTRACT: Reported herein is the one-pot synthesis of trifluoromethylated amines at room temperature using the bench-stable (Me₄ N)SCF₃ reagent and AgF. The method is rapid, operationally simple and highly selective. It proceeds via a formal umpolung reaction of the SCF₃ with the amine, giving quantitative formation of thiocarbamoyl fluoride intermediates within minutes that can readily be transformed to N-CF₃ . The mildness and high functional group tolerance render the method highly attractive for the late-stage introduction of trifluoromethyl groups on amines, as demonstrated herein for a range of pharmaceutically relevant drug molecules.

SUBMITTER: Scattolin T

PROVIDER: S-EPMC6680219 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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Efficient Synthesis of Trifluoromethyl Amines through a Formal Umpolung Strategy from the Bench-Stable Precursor (Me4 N)SCF3.

Scattolin Thomas T Deckers Kristina K Schoenebeck Franziska F

Angewandte Chemie (International ed. in English) 20161209 1

Reported herein is the one-pot synthesis of trifluoromethylated amines at room temperature using the bench-stable (Me4 N)SCF3 reagent and AgF. The method is rapid, operationally simple and highly selective. It proceeds via a formal umpolung reaction of the SCF3 with the amine, giving quantitative formation of thiocarbamoyl fluoride intermediates within minutes that can readily be transformed to N-CF3 . The mildness and high functional group tolerance r ...[more]

PMID: 27936300

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