Phosphine-Catalyzed Cross-Coupling of Benzyl Halides and Fumarates
Tingting Yan, Kaki Raveendra Babu, Yong Wu, Yang Li, Yuhai Tang, Silong Xu
Abstract
A phosphine-catalyzed olefinic cross-coupling between benzyl halides and fumarates is described, which affords trisubstituted alkenes in good yields and excellent E-selectivity under metal-free conditions. Mechanistic studies suggest a catalytic cycle involving phosphorus ylide formation, Michael addition, water-assisted hydrogen transfer, and phosphine elimination.
Topics & Concepts
PhosphineChemistryCatalysisHalideYlideCoupling reactionSelectivityOrganic chemistryCombinatorial chemistryAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization Methods