A cross-coupling of aldehydes with α-haloboronates has been achieved under dual nickel/photoredox catalysis system. Considering the easy preparation of α-haloboronates with our deoxygenative difunctionalization of carbonyls (DODC) strategy, this protocol provides a formal deoxygenative cross-coupling of aldehydes to one-carbon-prolonged ketone products. The mild conditions enabled good functional group tolerance and broad substrate applicability. The application of this method was presented via a tunable synthesis of two ketones with very similar skeletons from two same aldehydes.

Comprehensive Summary

Aldehydes are a kind of important synthons and reagents in organic synthesis. The efforts on transformations of aldehydes are highly rewarding and have always attracted considerable attention. Herein, a cross-coupling of aldehydes with α-haloboronates has been achieved under dual nickel/photoredox catalysis system. Considering the α-haloboronates can be easily obtained from aldehydes with our deoxygenative difunctionalization of carbonyls (DODC) strategy, this protocol provides a formal deoxygenative cross-coupling of aldehydes to one-carbon-prolonged ketone products. The mild conditions enabled good functional group tolerance and broad substrate applicability. The application of this method was presented via a tunable synthesis of two ketones with very similar skeletons from two same aldehydes.