Aerobic oxidative cleavage of C=C bond to carbonyl compound

A highly efficient and selective carbon-carbon double bonds cleavage of styrene compounds involving molecular oxygen was achieved using TBHP as a free radical initiator in diethylene glycol diethyl ether medium. Various styrene compounds, such as phenyl acrylic acids and its esters, 2-substituted 3-phenyl acrylic acids and its esters, chalcones, 4-phenyl-3-buten-2-one and bis(2-phenylvinyl) ketone, 5-benzylidene-1,3-dimethylpyrimidine-2,4,6-triones, could be effectively oxidized into the corresponding aryl carbonyl compounds, and the yield was up to 99%. A suitable mechanism was proposed. Gram-level synthesis further illustrated the practicality of our method.

Automated summary

A highly efficient and selective carbon-carbon double bonds cleavage of styrene compounds using TBHP as a free radical initiator in diethylene glycol diethyl ether medium was achieved, with yields up to 99%. The proposed mechanism was suitable and gram-level synthesis further demonstrated the practicality of the method.