Effect of solvent on catalytic performance of anhydrous catalyst in acetylene dimerization to monovinylacetylene

The production of monovinylacetylene (MVA) through Cu(I)-catalyzed acetylene dimerization reaction was performed in different reaction media. Based on the analyses of crystals precipitated from the catalyst solution and UV-Vis spectra of the catalysts, the reaction mechanism and solvent dependence were studied. The highest yield of MVA can be obtained when dimethylformamide is used as solvent because of its strong coordination ability to Cu(I). The activation of C≡C bond is presumed to be improved when the catalytic metal ion is coordinated by a solvent with less steric hindrance and electron-rich coordination atom. The results of the present study provide a possible way to accelerate the metal-catalyzed homogeneous reaction of alkyne substrates through careful selection of a solvent.

Graphical abstractThe electron density of catalytic atom Cu(I) is increased by coordination of solvent, which is better for activation of C≡C bond, and thus produce a positive effect on acetylene dimerization reaction.Figure optionsDownload full-size imageDownload as PowerPoint slide