Coupling is a synthesis of symmetric or cyclic bisacetylenes via a
coupling reaction of terminal alkynes. Mechanistically, the reaction is
similar to the Eglinton Reaction;
the difference being the use of catalytic copper(I), which is reoxidized
in the catalytic cycle by oxygen in the reaction medium.
Hay Coupling has several advantages as compared with the Glaser
Coupling. The copper-TMEDA complex used is soluble in a wider range of
solvents, so that the reaction is more versatile.
A recent modification enables the production of a range of unsymmetrical
L. Su, J. Dong, L. Liu, M. Sun, R. Qiu, Y. Zhou, S.-F. Yin, J. Am. Chem. Soc., 2016,
alternative is the Cadiot-Chodkiewicz Coupling which
also allows the preparation of
Efficient Copper(II) Acetate Catalyzed Homo- and Heterocoupling of Terminal
Alkynes at Ambient Conditions
K. Balaraman, V. Kesavan, Synthesis, 2010, 3461-3466.
Phase Separation As a Strategy Toward Controlling Dilution Effects in
Macrocyclic Glaser-Hay Couplings
A.-C. Bédard, S. K. Collins, J. Am. Chem. Soc., 2011,
Recyclable Polystyrene-Supported Copper Catalysts for the Aerobic Oxidative
Homocoupling of Terminal Alkynes
S. Yan, S. Pan, T. Osako, Y. Uozumi,
Synlett, 2016, 27, 1232-1236.
One-Pot Formation and Derivatization of Di- and Triynes Based on the
T. Luu, Y. Morisaki, N. Cunningham, R. R. Tykwinski, J. Org. Chem., 2007,
End-Cap Stabilized Oligoynes: Model Compounds for the Linear sp Carbon
T. Gibtner, F. Hampel, J.-P.Gisselbrecht, A. Hirsch,
Chem. Eur. J., 2002, 68, 408-432.