Stereospecific Cross-Coupling of Alkenylsilanolates with Aryl Chlorides

Significance

While the aryl-aryl cross-coupling reaction of aryl chlorides and arylboronic acids has become widely used, the same reaction of alkenylboronic acids is not as smooth, even in the presence of modern powerful catalysts, due to the intrinsically lower reactivity of these compounds. The use of alkenyl silanolates, which are stable, readily available crystalline compounds, is a good alternative, especially when a product with high stereoselectivity is required. The reactions between a broad variety of aryl or hetaryl chlorides and alkenyl silanolates lead to the cross-coupling products in excellent yields and stereoselectivities.