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A General Method for Two-Step Transamidation of Secondary Amides Using Commercially Available, Air- and
Guangrong Meng1, Peng Lei1, Michal Szostak1
1Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.
Organic Letters
|April 12, 2017
Abstract:
The first general method is reported for transamidation of secondary carboxamides catalyzed by Pd-NHC (NHC = N-heterocyclic carbene) complexes. Commercially available, air- and moisture-stable (NHC)Pd(R-allyl)Cl complexes can effect C-N cross-coupling of a wide range of N-Boc and N-Ts amides, obtained by selective amide N-functionalization, with non-nucleophilic anilines and sterically hindered amines in very good yields. The first use of versatile Pd-NHC complexes as catalysts is represented for transition-metal-catalyzed C(acyl)-N amination of amides by N-C activation.