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Regio- and Stereochemical Aspects of the Palladium-Catalyzed Desilylation-Arylation of Substituted Vinylsilanes
Authors:Alvisi Davide  Blart Errol  Bonini Bianca Flavia  Mazzanti Germana  Ricci Alfredo  Zani Paolo
Affiliation:Dipartimento di Chimica Organica "A. Mangini", Facoltà di Chimica Industriale, viale Risorgimento 4, I-40136 Bologna, Italy, and Laboratoire de Synthèse Organique, Faculté des Sciences et Techniques, rue de la Houssinière 2, F-44072 Nantes Cedex 03, France.
Abstract:The palladium-catalyzed desilylation-arylation of substituted vinylsilanes by p-iodoanisole in the presence of bidentate phosphine ligands is described. Apart from enhancing the rate of the reaction considerably, heteroatom-based functional groups in the vinylsilane moiety have a profound influence on the regiochemistry. A catalytic cycle for the chelation-controlled desilylation-arylation reaction involving five- and six-membered chelate rings is proposed.
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