Synthesis of Unsaturated Silyl Heterocycles via an Intramolecular Silyl-Heck Reaction

We report the synthesis of unsaturated silacycles via an intramolecular silyl-Heck reaction. Using palladium catalysis, silicon electrophiles tethered to alkenes cyclize to form five- and six-membered silicon heterocycles. The effects of alkene substitution and tether length on the efficiency and regioselectivity of the cyclizations are described. Finally, through the use of an intramolecular tether, the first examples of disubstituted alkenes in silyl-Heck reactions are reported.