Cyclization Reactions Involving Palladium-Catalyzed Carbene Insertion into Aryl Halides

Palladium is shown to catalyze the insertion of trimethylsilylmethylene into aryl halides, leading to benzylpalladium intermediates that cyclize to give indenylsilanes through carbopalladation of pendant alkenes or allenes. Allylsilanes generated through these processes are susceptible to protodesilylation in situ.