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  • Title: Nickel-Catalyzed Asymmetric Reductive Arylalkylation of Unactivated Alkenes.
    Author: Jin Y, Wang C.
    Journal: Angew Chem Int Ed Engl; 2019 May 13; 58(20):6722-6726. PubMed ID: 30888731.
    Abstract:
    Reported is an asymmetric reductive dicarbofunctionalization of unactivated alkenes. Under the catalysis of a Ni/BOX system, various aryl bromides, incorporating a pendant olefinic unit, were successfully reacted with an array of primary alkyl bromides in the presence of Zn as a reductant, furnishing a series of benzene-fused cyclic compounds bearing a quaternary stereocenter in high enantioselectivities. Notably, this reaction avoids the use of pregenerated organometallics and demonstrates high tolerance of sensitive functionalities. The preliminary mechanistic investigations reveal that this Ni-catalyzed reaction proceeds as a cascade consisting of migratory insertion and cross-coupling with a nickel(I)-mediated intramolecular 5-exo cyclization as the enantiodetermining step.
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