Diazene-Catalyzed Oxidative Alkyl Halide-Olefin Metathesis

The first platform for oxidative alkyl halide-olefin metathesis is described. The procedure employs diazenes as catalysts, which effect the cyclization of alkenyl alkyl halides to generate cyclic olefins and carbonyl products. The synthesis of phenanthrene, coumarin, and quinolone derivatives is demonstrated as well as the potential to apply this strategy to other electrophiles.