Cross-coupling

A coupling reaction in organic chemistry is a general term for a variety of reactions where two hydrocarbon fragments are coupled with the aid of a metal catalyst. In one important reaction type a main group organometallic compound of the type RM (R = organic fragment, M = main group centre) reacts with an organic halide of the type R'X with formation of a new carbon-carbon bond in the product R-R'

Richard F. Heck, Ei-ichi Negishi and Akira Suzuki were awarded the 2010 Nobel Prize in Chemistry for developing palladium catalyzed cross coupling reactions.

Broadly speaking, two types of coupling reactions are recognized:

The reaction mechanism generally begins with the oxidative addition of an organic halide to the catalyst. Subsequently, the second partner undergoes transmetallation, which places both coupling partners on the same metal center while eliminating the functional groups. The final step is reductive elimination of the two coupling fragments to regenerate the catalyst and give the organic product. Unsaturated organic groups couple more easily in part because they add readily. The intermediates are also less prone to beta-hydride elimination.

In one computational study, unsaturated organic groups were shown to undergo much easier coupling reaction on the metal center. The rates for reductive elimination followed the following order: vinyl-vinyl > phenyl-phenyl > alkynyl-alkynyl > alkyl-alkyl. The activation barriers and the reaction energies for unsymmetrical R-R′ couplings were found to be close to the averages of the corresponding values of the symmetrical R-R and R′-R′ coupling reactions; for example: vinyl-vinyl > vinyl-alkyl > alkyl-alkyl. Another mechanistic approach proposes that specifically in aqueous solutions, coupling actually occurs via a radical mechanism rather than a metal-assisted one. Most of the coupling reaction's mechanisms slightly vary from this generalized form.

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