Palladium-Catalyzed Sequential Three-Component Cross-Coupling to 1,3-Dienes: Employing Alkenes as Hydride and Alkenyl Donors.

This report discloses a novel Pd-catalyzed sequential three-component multiple reaction of alkenes, bromoalkynes, and boronic acids using alkenes as hydride and alkenyl donors, leading to highly stereoselective assembly of ( Z , E )-1,3-diene derivatives. Mechanistic studies demonstrate that the generation and reutilization of palladium hydride species are critical to the success of this transformation. In addition, the good functional group compatibility, late-stage modification, and investigation of photophysical properties of 1,3-diene products illustrate the synthetic value of this strategy.