Base-Promoted Stereoselective Hydroalkoxylation of Alkynes

Base-promoted and stereoselective synthesis of C(sp2)-O bond through the anti-Markovnikov addition of alcohols onto alkyne and has been discovered. Developed protocol tolerates a wide variety of functional groups to afford styryl ethers from commercially and economical available chemicals without using metal-catalyst. The reaction features selective synthesis of stereoisomers, which are readily obtained by subtle tuning of the reaction time. The proposed mechanism and significant role of the solvent were well established by deuterium labeling studies.