Synthesis of Carbamoyl Azides from Redox-Active Esters and TMSN ₃

An efficient method for construction of C-N bonds is reported here. The iron-catalyzed azidation of N-hydroxy phthalimide (NHP) esters provides a convenient approach for the synthesis of carbamoyl azides with good substrate scope and functional group tolerance. Both aryl carbon C(sp(2)) and alkyl carbon C(sp(3)) sources can be used deliver the carbamoyl azides. Mechanistic studies were conducted and a two-stage process was identified.