NHC-catalyzed Truce–Smiles rearrangement of N-aryl methacrylamides for the synthesis of trans-cinnamides

Abstract

Herein we describe a NHC-catalyzed Truce–Smiles rearrangement of N-aryl methacrylamides which enables the cleavage of an inert aryl C–N bond. A range of trans-cinnamides could be obtained by the direct construction of a C_(aryl)–C_(alkenyl) bond and functional groups such as Br, Cl, CN, and pyridinyl are compatible with NHC catalysis. The reaction features high atom-economy, transition-metal free catalysis, and easily available substrates.