Nickel-Catalyzed Heck-Type Alkenylation of Secondary and Tertiary [alpha]-Carbonyl Alkyl Bromides

Ni made it! A novel Heck-type reaction of secondary and tertiary [alpha]-carbonyl alkyl bromides, most likely involving a radical process, was achieved through the use of a nickel catalyst. Various substituted styrenes and 1,1-diaryl alkenes were utilized as substrates to easily construct [alpha]-alkenyl carbonyl compounds with tertiary or quaternary carbon centers. A catalytic cycle involving Ni super(I)/Ni super(II) is proposed based on our experimental results. EWG=electron-withdrawing group.