Oxidative organic electrochemistry: a novel intramolecular coupling of electron-rich olefins

Oxidative cyclization reactions are of interest because they allow for the generation of carbon-carbon bonds and the formation of rings without a loss in the overall functionality of a molecule. Organic electrochemistry would appear ideally suited for initiating such reactions because it can selectively oxidize electron-rich functional groups at preset potentials, under neutral conditions, and without the need for chemical reagents. Unfortunately, there exist only a few examples of anodic reactions that lead to direct carbon-carbon bond formation. In addition, only a handful of these reactions have been shown to be generally useful for initiating intramolecular cyclization reactions. The authors report herein their initial efforts to develop the anodic coupling of electron-rich olefins for such a purpose.