Coupling reaction

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A coupling reaction in organic chemistry is a general term for a variety of reactions
where two fragments are joined together with the aid of a metal catalyst. In one
important reaction type, a main group organometallic compound of the type R-M (R =
organic fragment, M = main group center) reacts with an organic halide of the type R'-X
with formation of a new carbon-carbon bond in the product R-R'. The most common
type of coupling reaction is the cross coupling reaction.
Broadly speaking, two types of coupling reactions are recognized:

 Heterocouplings combine two different partners, such as in the Heck reaction of

an alkene (RC=CH) and an alkyl halide (R'-X) to give a substituted alkene. Heterocouplings are
called cross-couplings.
 Homocouplings couple two identical partners, as in the Glaser coupling of
two acetylides (RC≡CH) to form a dialkyne (RC≡C-C≡CR).

Homo-coupling types[edit]
Coupling reactions are illustrated by the famous Ullmann reaction:

Reaction Year Reactant A Reactant B Reagent Remark

Na as
185
Wurtz reaction R-X sp3 R-X sp3 reducing
5
agent

Pinacol
185 R-HC=O or R-HC=O or various requires proton
coupling
9 R2(C=O) R2(C=O) metals donor
reaction

186 O2 as H-
Glaser coupling RC≡CH sp RC≡CH sp Cu
9 acceptor

Ullmann 190 high

Ar-X sp2 Ar-X sp2 Cu
reaction 1 temperatures

Cross-coupling types[edit]
Main article: cross-coupling reaction
An illustrative cross-coupling reaction is the Heck coupling of an alkene and an aryl halide:

Other notable examples of cross-coupling reactions include:

 The Grignard reaction

 Sonagashira cross-coupling
 Suzuki coupling
 The Buchwald-Hartwig reaction

Applications of Coupling Reactions

Some important applications of coupling reactions are listed below.

 Coupling reactions are employed in the synthesis of several pharmaceutical products.

 Many conjugated polymers are prepared via coupling reactions that involve the use of a
metal catalyst.
 The Suzuki coupling reaction (which is an important class of coupling reactions) is also used
in the synthetic production of complex compounds. For example, it is used in the production
of caparratriene, which is highly effective in the treatment of leukaemia.
 Many natural products can be obtained via certain coupling reactions. For example,
benzylisoquinoline alkaloids can be synthesized with the help of the Sonogashira cross-
coupling reaction.