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