Organosulphur and organoselenium compounds as ligands for catalytic systems in the Sonogashira coupling

Abstract

Sonogashira coupling is a reaction of aryl/vinyl halides with terminal alkynes. It is used for the synthesis of conjugated enynes. Generally, copper (Cu) is required as a mediator for this reaction. It requires a long reaction time, high catalyst loading, or expensive ligands. Recently, homogeneous, heterogeneous, and nanocatalysts have been developed using organosulphur and organoselenium compounds as building blocks. Preformed complexes of metals with organosulphur and organoselenium ligands are used for homogeneous catalysis. Heterogeneous catalytic systems have also been developed using Cu, Pd, and Ni as metals. The nanocatalytic systems (synthesized using such ligands) include copper selenides and stabilized palladium(0) nanospecies. This article aims to cover the developments in the field of the processes and techniques used so far to generate catalytically relevant organic ligands having sulphur or selenium donor sites, the utility of such ligands in the syntheses of homogeneous, heterogeneous, and nanocatalytic systems, and critical analysis of their application in the catalysis of this coupling reaction. The results of catalysis are analyzed in terms of the effects of the S/Se donor, halogen atom of aryl halide, the effect of the presence/absence of electron-withdrawing or electron-donating groups or substituents on the aromatic ring of haloarenes/substituted phenylacetylenes, as well as the position (ortho or para) of the substitution. Substrate scope is discussed for all the kinds of catalysis. The supremacy of heterogeneous and nanocatalytic systems indicates promising future prospects.