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NHC-catalyzed Truce-Smiles rearrangement of N-aryl methacrylamides for the synthesis of trans-cinnamides. 2021
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, China. zhoubw@zjut.edu.cn.
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.
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