Control of chemo-, regio-, and stereoselectivities in ligand-free Pd-catalyzed oxidative Heck reactions of arylboronic acids or alkenylboronate with allyl esters.Org Lett. 2009 Jul 16; 11(14):2980-3.OL
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.