Deoxygenative Arylboration of Aldehydes via Copper and Nickel/Photoredox Catalysis

Abstract

Deoxygenative difunctionalization of carbonyls represents a convenient route to construct complex molecules considering the readily available aldehyde and ketone compounds. The present approaches typically rely on strategies via carbene, carbanion, or carbocation equivalents. Herein, combined with dual nickel/photoredox catalysis regime, we developed a strategy through a radical intermediate to achieve the deoxygenative arylboration of aldehydes. Compared with the known patterns of carbon–oxygen (C–O) bond transformations, this coupling of C-OBPin unit opens a direction for this chemistry. A wide variety of substrates bearing a diverse set of functional groups were compatible with this method under very mild conditions (visible light, ambient temperature, no strong base) to afford the benzylic boronic esters, which have important versatilities in organic synthesis.