Olefination of Alcohols and Alkyl Halides via Oxidative Alkyl Electrophile–Olefin Metathesis

A method for the olefination of benzylic halides and alcohols with unactivated alkenes via oxidative alkyl electrophile-olefin metathesis (AEOM) is described. The procedure employs a simple bicyclic diazene to promote the formation of a new carbon-carbon double bond between an alcohol or alkyl halide and an olefin through a sequence of [3 + 2] cycloaddition and cycloreversion steps. The synthesis of substituted styrenes and cinnamate esters is demonstrated.