Dual Catalysis Relay: Coupling of Aldehydes and Alkenes Enabled by Visible-Light and NHC-Catalyzed Cross-Double C-H Functionalizations

Direct functionalizations of two distinct inert C-H bonds represent the most ideal ways to construct C-C bonds. Herein, we report an intermolecular vinylation of aldehydes using alkenes as the vinylating reagents through sequential two-fold C-H functionalizations. The merging of visible light and N-heterocyclic carbene catalysis allows for the coupling of alkenes with aldehydes through a dual catalysis relay enabled cross-dehydrogenative coupling mechanism. The use of diphenoquinone is essential for the success of this reaction, which plays an intriguing two-fold role in the reaction, as an electron acceptor as well as a radical reservoir for the radical coupling enabling the C-C forming process.

Automated summary

This translation describes a method of intermolecular vinylation of aldehydes using alkenes as the vinylating reagents through sequential two-fold C-H functionalizations and a dual catalysis relay enabled cross-dehydrogenative coupling mechanism.