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

Patrick Wagner; Mihaela Gulea; Jean Suffert; Morgan Donnard

doi:10.1002/chem.201701736

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

Chemistry. 2017 Jun 1;23(31):7458-7462. doi: 10.1002/chem.201701736. Epub 2017 May 15.

Authors

Patrick Wagner¹, Mihaela Gulea¹, Jean Suffert¹, Morgan Donnard¹

Affiliation

¹ Université de Strasbourg, CNRS (LIT UMR 7200), 67000, Strasbourg, France.

PMID: 28422328
DOI: 10.1002/chem.201701736

Abstract

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.

Keywords: carbopalladation; domino sequence; palladium; silacycle; vinylsilanes.