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. The reaction product is a di-acetylene or di-alkyne.
The reaction mechanism involves deprotonation by base of the acetylenic proton followed by formation of a copper(I) acetylide. A cycle of oxidative addition and reductive elimination on the copper center then creates a new carbon-carbon bond.
Related couplings are the Glaser coupling and the Eglinton coupling.
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 NBS and silver nitrate:
- Glaser coupling - Another alkyne coupling reaction catalysed by copper (I).
- Sonogashira coupling - Pd/Cu catalysed coupling of an alkyne with an aryl or vinyl halide
- Castro–Stephens coupling - A cross-coupling reaction between a copper(I) acetylide and an aryl halide
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- Graham E. Jones, David A. Kendrick, and Andrew B. Holmes (1993). "1,4-Bis(trimethylsilyl)buta-1,3-diyne". Org. Synth.; Coll. Vol. 8, p. 63