Gold-catalyzed intramolecular allylation of silyl alkynes induced by silane alcoholysis.
The activation of alkynyl allyl silanes with a cationic gold catalyst in the presence of alcohols provides vinyl silanes that contain the allyl group at the beta-position and the alkoxysilyl group in cis-orientation. The bond reorganization process is most consistent with the involvement of a carbocationic intermediate, which undergoes a nucleophilic attack by an alcohol selectively at the silicon center. The cis-vinyl silyl ether products can be further elaborated by ring-closing and cross metathesis to form more substituted 1,4-dienyl silanes.
Park
Sangho
S
Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA.
Lee
Daesung
D
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*
D000480:Alkynes; D012821:Silanes; D006046:Gold