Zinc-catalyzed dehydrogenative coupling of primary alcohols and secondary/benzyl phosphine oxides for alkene synthesis

Abstract

A zinc-catalyzed method has been developed for the direct conversion of primary alcohols into alkenes under acceptorless dehydrogenation conditions. Utilizing a simple and Earth-abundant zinc catalyst, this approach enables the dehydrogenative coupling of primary alcohols with either diphenylphosphine oxide (to generate symmetric alkenes) or benzyl phosphine oxides (to generate asymmetric alkenes), affording a diverse range of alkenes in moderate to high yields with (E)-selectivity. This strategy provides a promising facile route for alkene synthesis directly from readily accessible alcohols, as evidenced by gram-scale reactions and the preparation of the biologically active compounds DMU-212 and resveratrol.