Highly stereoselective synthesis of E-4-chlorostilbene and its derivatives via tandem cross-metathesis (or silylative coupling) and Hiyama coupling

Cross-metathesis of 4-chlorostyrene with vinylsilanes in the presence of second generation of Grubbs catalyst [Cl2(PCy3)(IMesH2)Ru(CHPh)] or silylative coupling in the presence of [RuH(Cl)(CO)(PPh3)3] followed by palladium-catalysed Hiyama coupling have been proved convenient and effective methods for stereoselective synthesis of unsymmetrical stilbenoids.

Highly effective new tandem reactions: cross-metathesis–Hiyama coupling (CM–HC) and silylative coupling–Hiyama coupling (SC–HC) lead to stereoselective synthesis of unsymmetrical stilbenoids.Figure optionsDownload as PowerPoint slide