Cadiot-Chodkiewicz Coupling
The Cadiot–Chodkiewicz coupling is an organic chemical reaction that involves the coupling of a terminal alkyne with a haloalkyne, catalyzed by a copper(I) salt such as copper(I) bromide, often in the presence of an amine base[1][2][4]. This reaction produces a 1,3-diyne or di-alkyne as the product[1][4]. The mechanism of the reaction includes the deprotonation of the terminal alkyne by the base, followed by the formation of a copper(I) acetylide. Subsequently, a cycle of oxidative addition and reductive elimination at the copper center forms a new carbon-carbon bond[1][4].
The Cadiot–Chodkiewicz coupling is selective and typically yields a single product, contrasting with the Glaser coupling, which can produce a mixture of coupling products[1]. This selectivity makes the Cadiot–Chodkiewicz coupling valuable for the synthesis of unsymmetrical diynes, which have significant biological, optical, and electronic properties[3][6][11][14].
Recent developments in the Cadiot–Chodkiewicz coupling have focused on improving the reaction's efficiency, selectivity, and yield[3][6][11][14]. These advancements have expanded the scope of the reaction, enabling the synthesis of a wide range of aliphatic and aromatic diacetylenic compounds with applications in pharmaceuticals, biology, and materials science[3][6][11][14].
Citations:
[1] https://en.wikipedia.org/wiki/Cadiot%E2%80%93Chodkiewicz_coupling
[2] https://www.sciencedirect.com/topics/chemistry/cadiot-chodkiewicz-coupling
[3] https://pubs.rsc.org/en/content/articlelanding/2015/ob/c5ob00697j
[4] https://www.chemeurope.com/en/encyclopedia/Cadiot-Chodkiewicz_coupling.html
[5] https://www.youtube.com/watch?v=ACzRpyjRUU4
[6] https://pubmed.ncbi.nlm.nih.gov/26008847/
[7] https://www.wikiwand.com/en/Cadiot%E2%80%93Chodkiewicz_coupling
[8] https://www.youtube.com/watch?v=1MlQu5CQVZ4
[9] https://www.researchgate.net/publication/336166381_Recent_Trends_and_Applications_of_Cadiot-Chodkiewicz_Reaction
[10] https://academic-accelerator.com/encyclopedia/cadiot-chodkiewicz-coupling
[11] https://pubs.rsc.org/en/content/articlehtml/2015/ob/c5ob00697j
[12] https://pubs.acs.org/doi/abs/10.1021/acs.orglett.3c03314
[13] https://alchetron.com/Cadiot%E2%80%93Chodkiewicz-coupling
[14] https://pubs.rsc.org/en/content/articlelanding/2019/ob/c9ob01757g
[15] https://www.wikidata.org/wiki/Q903015
[16] https://www.researchgate.net/publication/276150276_Recent_developments_and_applications_of_the_Cadiot-Chodkiewicz_reaction