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Control of chemo-, regio-, and stereoselectivities in ligand-free Pd-catalyzed oxidative Heck reactions of arylboronic acids or alkenylboronate with allyl esters.

A ligand-free Pd-catalyzed highly selective oxidative Heck reaction of organoboronic acids with allyl esters was developed. Beta-H elimination is highly chemoselectively controlled, leading to gamma-substituted allyl esters, which is contrary to the traditional Heck-type reactions of allyl esters. Moreover, the regio- and stereoselectivities are also high due to the chelation between O and Pd atoms.