by Soumik Biswas and Daniel J. Weix*
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.
Journal of the American Chemical Society
Article first published online: 18 AUG 2013
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