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>i</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