Formal β‐C−H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis

Abstract

Abstractα‐C−H‐functionalization of ketones and aldehydes has been intensively explored in organic synthesis. The functionalization of unactivated β‐C−H bonds in such carbonyl compounds is less well investigated and developing a general method for their β‐C−H arylation remains challenging. Herein we report a method that uses cooperative nickel and photoredox catalysis for the formal β‐C−H arylation of aldehydes and ketones with (hetero)aryl bromides. The method features mild conditions, remarkable scope and wide functional group tolerance. Importantly, the introduced synthetic strategy also allows the β‐alkenylation, β‐alkynylation and β‐acylation of aldehydes under similar conditions. Mechanistic studies revealed that this transformation proceeds through a single electron oxidation/Ni‐mediated coupling/reductive elimination cascade.