Heterogeneous allylsilylation of aromatic and aliphatic alkenes catalyzed by proton-exchanged montmorillonite

Org Lett. 2010 Apr 2;12(7):1508-11. doi: 10.1021/ol100228t.

Abstract

Allylsilylation of an alkene is the only known procedure to install both silyl and allyl groups onto a carbon-carbon double bond directly. Proton-exchanged montmorillonite showed excellent catalytic performances for the allylsilylation of alkenes. For example, the reaction of p-chlorostyrene with allyltrimethylsilane proceeded smoothly to afford the corresponding allylsilylated product in 95% yield. We also attempted to isolate the reaction intermediate on the montmorillonite surface to investigate the reaction mechanism.