Regio- and Stereochemical Aspects of the Palladium-Catalyzed Desilylation-Arylation of Substituted Vinylsilanes.
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.
Alvisi
Davide
D
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.
Blart
Errol
E
Bonini
Bianca Flavia
BF
Mazzanti
Germana
G
Ricci
Alfredo
A
Zani
Paolo
P