Copper-Mediated Selective C–H Activation and Cross-Dehydrogenative C–N Coupling of 2′‑Aminoacetophenones

2013-11-15T00:00:00Z (GMT) by Andivelu Ilangovan Gandhesiri Satish
Isatins were obtained by cross-dehydrogenative C–N annulation and dealkylative C–N annulation of 2′-N-aryl/alkylaminoacetophenones and 2′-N,N-dialkylaminoacetophenones respectively in the presence of Cu(OAc)2·H2O/NaOAc/air. However, on reaction with CuBr, 2′-N-benzylaminoacetophenones underwent selective oxidation of an α-methylene group of amine rather than the 2-acetyl group to provide corresponding benzamides exclusively. Base played an important role in selective oxidation by lowering the temperature and time.