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  • Title: Mechanism and selectivity in nickel-catalyzed cross-electrophile coupling of aryl halides with alkyl halides.
    Author: Biswas S, Weix DJ.
    Journal: J Am Chem Soc; 2013 Oct 30; 135(43):16192-7. PubMed ID: 23952217.
    Abstract:
    The direct cross-coupling of two different electrophiles, such as an aryl halide with an alkyl halide, offers many advantages over conventional cross-coupling methods that require a carbon nucleophile. Despite its promise as a versatile synthetic strategy, a limited understanding of the mechanism and origin of cross selectivity has hindered progress in reaction development and design. Herein, we shed light on the mechanism for the nickel-catalyzed cross-electrophile coupling of aryl halides with alkyl halides and demonstrate that the selectivity arises from an unusual catalytic cycle that combines both polar and radical steps to form the new C-C bond.
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