Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift

Abstract

Organoboron "ate" complexes undergo a net vinyl insertion reaction to give 1,1-disubstituted alkenyl boronic esters when treated with stoichiometric allyl acetate and a palladium catalyst. Reactions that employ vinyllithium afforded good to excellent yields after one hour, while reactions that employ vinylmagnesium chloride furnished modest to good yields after 18 hours.

Keywords: allyl complexes; boron; homogeneous catalysis; palladium.