Regioselective synthesis of multisubstituted benzenes by palladium-catalyzed intermolecular reaction of β-iodo-β-silylstyrenes with alkynes.

The Pd-catalyzed reaction between β-iodo-β-silylstyrenes and terminal alkynes in i-Pr2NEt gave 1,2,3,5-tetrasubstituted benzenes with complete regioselection. The use of certain silylacetylenes as alkynes enabled efficient synthesis of 1,3,5-trissilyl-2-arylbenzenes, which could be transformed into other multisubstituted benzenes by displacement of the silyl groups.