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.
Su
Yijin
Y
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China.
Jiao
Ning
N
D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000498:Allyl Compounds; D001897:Boronic Acids; D004952:Esters; D010165:Palladium