Nickel-catalyzed coupling of alkyne-tethered vinylcyclopropanes and allyl chloride

A nickel-catalyzed coupling of the alkyne-tethered vinylcyclopropanes 1 (VCPs) with the allyl chloride 2 has been developed: the reaction proceeds via the addition of (pi-allyl)nickel species to the alkyne moiety, the incorporation of the pendant VCP, and then beta-syn elimination of the cyclopropyl carbon-carbon bond, to stereoselectively give 3 with an (E)-1,3-diene.