Pd-catalyzed Suzuki cross-coupling reactions of glycerol arylboronic esters

Abstract

Abstract The reaction of glycerol with phenylboronic acid provided a mixture of cyclic glycerol esters, glycerol 1,2-phenylboronate (80%), and glycerol 1,3-phenylboronate (20%). The latter two products were formed from the esterification of the 1,2- and 1,3-hydroxyl groups, respectively. The glycerol phenylboronates were applied to the Pd-catalyzed Suzuki cross-coupling reactions with aryl halides, affording the corresponding biphenyl products in high yields. Excess glycerol phenylboronate was not required, and the Suzuki coupling reaction employed a simple catalyst precursor prepared in situ from palladium acetate and triphenylphosphine under mild reaction conditions. Arylboronic acid and pinacol arylboronic ester yielded similar results under the optimized reaction protocol.