上海
Glaser偶联是通过两个端基炔合成对称二炔或环状二炔的常用反应。机理上与Eglinton 反应类似，不同的是此反应用一价铜作为催化剂，通过反应中加入氧气重新氧化完成催化循环。
与之类似的Hay偶联相比Glaser偶联有很多优点，此反应中用到的Cu-TMEDA络合物催化剂可以溶于很多溶剂，所以反应应用性更广。
Cadiot-Chodkiewicz 偶联可以合成非对称的二炔可以作为此反应的互补反应，很有价值。
反应机理
图片来源：https://cheminfographic.wordpress.com/2018/02/18/74-glaser-hay-coupling-1869/
反应实例
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, 133, 19976-19981.
One-Pot Formation and Derivatization of Di- and Triynes Based on the Fritsch-Buttenberg-Wiechell Rearrangement
T. Luu, Y. Morisaki, N. Cunningham, R. R. Tykwinski, J. Org. Chem., 2007, 72, 9622-9629.
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.
L. Su, J. Dong, L. Liu, M. Sun, R. Qiu, Y. Zhou, S.-F. Yin, J. Am. Chem. Soc., 2016, 138, 12348-12351.
参考资料
Organic Chemistry Portal：Glaser Coupling、Hay Coupling
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