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  • Title: Regioselective Alkylative Cross-Coupling of Remote Unactivated C(sp3)-H Bonds.
    Author: Thullen SM, Treacy SM, Rovis T.
    Journal: J Am Chem Soc; 2019 Sep 11; 141(36):14062-14067. PubMed ID: 31478370.
    Abstract:
    The functionalization of unactivated C(sp3)-H bonds poses a significant challenge due to their ubiquity and relative similarity in most organic frameworks. Herein, we describe the use of a combined photoredox and nickel catalytic system for the regioselective C(sp3)-C(sp3) coupling of unactivated C(sp3)-H bonds and alkyl bromides. Positional selectivity is dictated by a 1,5-hydrogen atom transfer (HAT) reaction by a pendent amide. Interception of this radical by a Ni catalyst allows distal alkylation to occur in good yield and excellent selectivity.
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