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Cadiot–Chodkiewicz coupling

Reaction in organic chemistry

Wladyslaw Chodkiewicz The Cadiot–Chodkiewicz coupling in organic chemistry is a coupling reaction between a terminal alkyne and a haloalkyne catalyzed by a copper(I) salt such as copper(I) bromide and an amine base.Cadiot, P.; Chodkiewicz, W. In Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; pp. 597–647. The reaction product is a 1,3-diyne or di-alkyne.

The reaction mechanism involves deprotonation by base of the terminal alkyne proton followed by formation of a copper(I) acetylide. A cycle of oxidative addition and reductive elimination on the copper centre then creates a new carbon-carbon bond.

Scope

Unlike the related Glaser coupling the Cadiot–Chodkiewicz coupling proceeds selectively and will only couple the alkyne to the haloalkyne, giving a single product. By comparison the Glaser coupling would simply produce a distribution of all possible couplings. In one study the Cadiot–Chodkiewicz coupling has been applied in the synthesis of acetylene macrocycles starting from cis-1,4-diethynyl-1,4-dimethoxycyclohexa-2,5-diene. This compound is also the starting material for the dibromide through N-bromosuccinimide (NBS) and silver nitrate:

The coupling reaction itself takes place in methanol with piperidine, the hydrochloric acid salt of hydroxylamine and copper(I) bromide.

References

Chodkiewicz, W. Ann. Chim. Paris '''1957''', 2, 819–69.
(2006). "Synthesis of 1,4-Cyclohexadiene-Based Acetylenic Macrocycles with Cadiot–Chodkiewicz Coupling. Structure of a Tub-Shaped Tetrameric Container". [[Journal of Organic Chemistry]].

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