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43.1.1.1.1 Method 1: Copper-Promoted Oxidative Homocoupling of Terminal Alkynes

DOI: 10.1055/sos-SD-043-00002

Hirsch, A.; Vostrowsky, O.Science of Synthesis, (20084338.

Acetylides with transition metalcarbon σ-bonds are suited for CC coupling reactions, and as long ago as 1869 Glaser observed that the smooth oxidative dimerization of copper(I) phenylacetylide (2), prepared from phenylacetylene (1), takes place in the presence of air and gives 1,4-diphenylbuta-1,3-diyne (3) (Scheme 1).[‌50‌] This discovery has since made metal-catalyzed oxidative alkyne dimerization one of the most relevant and attractive CC bond-forming transformations available to modern chemists.

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