Treatment of silyl enol ethers with 1-alkynes in the presence of SnCl4-Bu3N gave conjugated enones with (E)-configuration. This new C-C bond formation reaction between an enolate derivative and an unactivated acetylene involves a carbostannylation at the carbon-carbon triple bond. When phenols were subjected to the reaction in place of silyl enol ethers, ortho-alkenylation proceeded. Notably, ortho-vinylphenol was obtained by treating phenol with ethyne. The transformation described here convertes aromatic C-H bonds directly to C-CH=CH2 bonds.
ASJC Scopus subject areas
- Chemical Engineering(all)