Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins

The dealkenylative alkenylation of alkene C(sp(3))-C(sp(2)) bonds has been an unexplored area for C-C bond formation. Herein 64 examples of beta-alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with beta-nitrostyrenes by ozone/Fe-II-mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso-moracin and the drug (E)-metanicotine.