N-Heterocyclic nitrenium-catalyzed photoreductive radical-polar crossover for alkene dicarbofunctionalization

Abstract

The photoredox radical-polar crossover paradigm is a valuable tool for 1,2-difunctionalization of alkenes. However, the use of unactivated alkyl halides as radical precursors remains far less developed. Here, we report a photoreductive N-heterocyclic nitrenium-catalyzed radical-polar crossover for the 1,2-dicarbofunctionalization of alkenes by using unactivated alkyl and aryl iodides. These reactions can be carried out under simple, transition-metal-free conditions with easily obtainable materials such as alkyl/aryl halides, alkenes, and aldehydes. The reactions exhibit a broad range of substrate compatibility and good tolerance towards functional groups. This approach offers a new tool to unlock the compatibility of carbon skeletons.