Tetrahedron 2018-02-25

Copper(II)/Palladium(II) catalysed highly selective cross-coupling of terminal alkynes in supercritical carbon dioxide

Yunlong Wang, Quanling Suo, Limin Han, Linlin Guo, Yaqi Wang, Fawang Li

Index: 10.1016/j.tet.2018.02.060

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Abstract

An efficient protocol for the synthesis of unsymmetrical 1,3-diynes was developed using supercritical carbon dioxide (ScCO2) as the solvent. The direct coupling of two different terminal alkynes is catalysed by a bimetallic catalyst, CuCl2·2H2O/Pd(NH3)4Cl2·H2O, in the presence of the base tetramethylethylenediamine (TMEDA) and O2. In pure ScCO2, our bimetallic catalytic system maintains high activity over a wide substrate scope to provide unsymmetrical 1,3-diynes in good to excellent yields. In the proposed reaction mechanism, the synergistic cooperation between copper(II) and palladium(II) centres is responsible for the superior selectivity of the cross-coupling.

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