N-Heterocyclic Carbenes in Late Transition Metal Catalysis

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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Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides

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Richard D. Stauffer

Papers

Alkenylaryl compounds of nickel(II) and palladium(II). Influence of the transition metal on ligand proton chemical shifts

Nickel-promoted methylvinylcyclopropane rearrangements. Mechanistic relevance to the cis-1,4-hexadiene to 2-methyl-1,3-pentadiene isomerization

Nickel-catalyzed skeletal rearrangements of 1,4-dienes

Homogeneous catalysis of diene rearrangements via a carbon-metal .beta. elimination

Importance of the transition metal in the catalysis of a diene rearrangement