REGIOCHEMICAL AND STEREOCHEMICAL ASPECTS OF THE PALLADIUM-CATALYZED DESILYLATION-ARYLATION OF SUBSTITUTED VINYLSILANES

Authors
ALVISI D BLART E BONINI BF MAZZANTI G RICCI A ZANI P
Citation
D. Alvisi et al., REGIOCHEMICAL AND STEREOCHEMICAL ASPECTS OF THE PALLADIUM-CATALYZED DESILYLATION-ARYLATION OF SUBSTITUTED VINYLSILANES, Journal of organic chemistry, 61(20), 1996, pp. 7139-7146
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
20
Year of publication
1996
Pages
7139 - 7146
Database
ISI
SICI code
0022-3263(1996)61:20<7139:RASAOT>2.0.ZU;2-E
Abstract
The palladium-catalyzed desilylation-arylation of substituted vinylsil anes by p-iodoanisole in the presence of bidentate phosphine ligands i s described. Apart from enhancing the rate of the reaction considerabl y, heteroatom-based functional groups in the vinylsilane moiety have a profound influence on the regiochemistry. A catalytic cycle for the c helation-controlled desilylation-arylation reaction involving five- an d six-membered chelate rings is proposed.