Cadiot-Chodkiewicz Coupling

The copper(I)-catalyzed coupling of a terminal alkyne and an alkynyl halide offers access to unsymmetrical bisacetylenes.

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Mechanism of the Cadiot-Chodkiewicz Coupling

Recent Literature

Copper(I) Iodide Catalyzed Cross-Coupling Reaction of Terminal Alkynes with 1-Bromoalkynes: A Simple Synthesis of Unsymmetrical Buta-1,3-diynes
S. Wang, L. Yu, P. Li, L. Meng, L. Wang, Synthesis, 2011, 1541-1546.

Iron-Catalyzed Cadiot-Chodkiewicz Coupling with High Selectivity in Water under Air
Y.-A. Liao, W.-S. Peng, L.-J. Liu, T.-Y. Ye, J.-H. Fu, Y.-T. Chan, F.-Y. Tsai, J. Org. Chem., 2022, 87, 13698-13707.

Synthesis of 1,3-Diynes via Cadiot-Chodkiewicz Coupling of Volatile, in Situ Generated Bromoalkynes
P. C. Knutson, H. E. Fredericks, E. M. Ferreira, Org. Lett., 2018, 20, 6845-6849.

Bulky Trialkylsilyl Acetylenes in the Cadiot-Chodkiewicz Cross-Coupling Reaction
J. P. Marino, H. N. Nguyen, J. Org. Chem., 2002, 67, 6841-6844.

End-Cap Stabilized Oligoynes: Model Compounds for the Linear sp Carbon Allotrope Carbyne
T. Gibtner, F. Hampel, J.-P.Gisselbrecht, A. Hirsch, Chem. Eur. J., 2002, 68, 408-432.