Lewis Acid Catalyzed Stereoselective Carbosilylation. Intramolecular trans-Vinylsilylation and trans-Arylsilylation of Unactivated Alkynes

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Abstract
Intramolecular trans-vinylsilylation using silicon-tethered alkynylvinylsilanes 3b − c was catalyzed dramatically by Lewis acids such as EtAlCl2 to give the corresponding six-membered silacycles 4b − c in high yields. The reaction proceeded via an exo-mode cyclization. In addition to the vinylsilylation, the intramolecular trans-arylsilylations using carbon-tethered alkynylarylsilanes 8a − b were also catalyzed by Lewis acids such as HfCl4 to give six- and seven-membered cyclic (E)-vinylsilanes 9a − b, respectively. The cyclization of silicon-tethered substrates 13a − d afforded five- and six-membered silacycle products 14a − d in low to high yields. All arylsilylation reactions proceeded via an exo-mode fashion exclusively.

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