Iron-catalysed asymmetric carboazidation of styrenes

Abstract

Carboazidation of olefins is an efficient process to convert hydrocarbons directly into nitrogen-containing molecules. Such chemicals find broad applications in medicine and material sciences. Despite the fast development of carboazidation reactions, asymmetric radical carboazidations are still elusive. Here, we report a radical asymmetric carboazidation of olefins via an iron-catalysed group transfer mechanism. The method affords valuable chiral halogenated organoazides from inexpensive industrial chemical feedstocks. This radical azidation reaction is supported by mechanistic studies and should inspire further development of enantioselective radical reactions. The carboazidation of olefins represents an effective strategy to introduce both carbon and nitrogen substituents into hydrocarbons, but asymmetric versions of this reaction remain elusive. Now, an iron-catalysed asymmetric radical carboazidation is introduced that yields chiral halogenated organoazides in high enantiomeric ratios.