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Synthesis of Benzo[c]silole Derivatives Bearing a Tetrasubstituted Exocyclic C=C Double Bond by Palladium-Catalyzed Domino Reactions.

The synthesis of diversely substituted 2,3-dihydro-benzo[c]siloles through an unprecedented palladium-catalyzed domino sequence is reported, involving a cyclocarbopalladation of an internal silylalkyne. This reaction proceeds with complete stereoselectivity to lead to a fully substituted exocyclic C=C double bond. Notably, the overall domino sequence appears to be crucial to obtain the desired cyclic vinylsilanes.