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Efficient Synthesis of Trifluoromethyl Amines through a Formal Umpolung Strategy from the Bench‐Stable Precursor (Me 4 N)SCF 3
Author(s) -
Scattolin Thomas,
Deckers Kristina,
Schoenebeck Franziska
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201609480
Subject(s) - umpolung , trifluoromethyl , reagent , chemistry , functional group , combinatorial chemistry , amine gas treating , formal synthesis , molecule , organic chemistry , catalysis , nucleophile , polymer , alkyl
Reported herein is the one‐pot synthesis of trifluoromethylated amines at room temperature using the bench‐stable (Me 4 N)SCF 3 reagent and AgF. The method is rapid, operationally simple and highly selective. It proceeds via a formal umpolung reaction of the SCF 3 with the amine, giving quantitative formation of thiocarbamoyl fluoride intermediates within minutes that can readily be transformed to N‐CF 3 . 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.