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Mechanism and selectivity in nickel-catalyzed cross-electrophile coupling of aryl halides with alkyl halides.

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.

SUBMITTER: Biswas S

PROVIDER: S-EPMC3946589 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Mechanism and selectivity in nickel-catalyzed cross-electrophile coupling of aryl halides with alkyl halides.

Biswas Soumik S Weix Daniel J DJ

Journal of the American Chemical Society 20131021 43

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 ...[more]

PMID: 23952217

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