Ceric Ammonium Nitrate (CAN) Catalyzed Modification of Ketones <i>via</i> Two C–C Bond Cleavages with the Retention of the Oxo-Group

Abstract

A simple ceric ammonium nitrate (CAN) catalyzed functionalization of ketones through double C-C bond cleavage strategy has been disclosed. This reaction provides a mild, practical method toward carbamoyl azides, which are versatile intermediates and building blocks in organic synthesis. Based on relevant mechanistic studies, a unique and plausible C-C bond and N-O bond cleavage process is proposed, where the oxyamination intermediate plays an important role in this reaction.