Catalytic Intermolecular Tail-to-Tail Hydroalkenylation of Styrenes with α Olefins: Regioselective Migratory Insertion Controlled by a Nickel/N-Heterocyclic Carbene

Making head or tail of it: The first single-operation, highly selective intermolecular tail-to-tail hetero-hydroalkenylation from two readily available monosubstituted alkenes is described (see scheme; IPr=1,3-Bis(2,6-di- isopropylphenyl)imidazol-2-ylidene). The reaction is catalyzed by the proposed [(IPr)NiH]OTf species. The method allows the use of more common and structurally diverse α olefins as substrates, which were previously not compatible with known methods. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.