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  • Title: Highly selective nickel-catalyzed gem-difluoropropargylation of unactivated alkylzinc reagents.
    Author: An L, Xu C, Zhang X.
    Journal: Nat Commun; 2017 Nov 13; 8(1):1460. PubMed ID: 29133781.
    Abstract:
    In spite of the important applications of difluoroalkylated molecules in medicinal chemistry, to date, the reaction of difluoroalkylating reagents with unactivated, aliphatic substrates through a controllable manner remains challenging and has not been reported. Here we describe an efficient nickel-catalyzed cross-coupling of unactivated alkylzinc reagen\ts with gem-difluoropropargyl bromides. The reaction proceeds under mild reaction conditions with high efficiency and excellent regiochemical selectivity. Transformations of the resulting difluoroalkylated alkanes lead to a variety of biologically active molecules, providing a facile route for applications in drug discovery and development. Preliminary mechanistic studies reveal that an alkyl nickel intermediate [Ni(tpy)alkyl] (tpy, terpyridine) is involved in the catalytic cycle.
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