The coupling of aryl or vinyl halides with terminal acetylenes catalysed by palladium and other transition metals, commonly termed as Sonogashira cross-coupling reaction, is one of the most important and widely used sp2–sp carbon–carbon bond formation reactions in organic synthesis, frequently employed in the synthesis of natural products, biologically active molecules, heterocycles, molecular electronics, dendrimers and conjugated polymers or nanostructures. This critical review focuses on developments in the Sonogashira reaction achieved in recent years concerning catalysts, reaction conditions and substrates (352 references).

Recent advances in Sonogashira reactions

Copper-free PdCl2/PPh3-catalyzed Sonogashira coupling reaction of aryl bromides with terminal alkynes in water

Sonogashira coupling reactions in biodegradable ionic liquids derived from nicotinic acid

Ionic liquids (ILs) have unique physicochemical properties that make them advantageous for catalysis, such as low vapor pressure, non-flammability, high thermal and chemical stabilities, and the ability to enhance the activity and stability of (bio)catalysts. ILs can improve the efficiency, selectivity, and sustainability of bio(transformations) by acting as activators of enzymes, selectively dissolving substrates and products, and reducing toxicity. They can also be recycled and reused multiple times without losing their effectiveness. ILs based on imidazolium cation are preferred for structural organization aspects, with a semiorganized layer surrounding the catalyst. ILs act as a container, providing a confined space that allows modulation of electronic and geometric effects, miscibility of reactants and products, and residence time of species. ILs can stabilize ionic and radical species and control the catalytic activity of dynamic processes. Supported IL phase (SILP) derivatives and polymeric ILs (PILs) are good options for molecular engineering of greener catalytic processes. The major factors governing metal, photo-, electro-, and biocatalysts in ILs are discussed in detail based on the vast literature available over the past two and a half decades. Catalytic reactions, ranging from hydrogenation and cross-coupling to oxidations, promoted by homogeneous and heterogeneous catalysts in both single and multiphase conditions, are extensively reviewed and discussed considering the knowledge accumulated until now.

Ionic Liquids in Metal, Photo-, Electro-, and (Bio) Catalysis.

The catalytic activities of three N-methylimidazole-based phosphine ligands in the Suzuki coupling reaction were tested using PdCl2 as the catalyst. The results showed all three phosphine ligands exhibited excellent activity towards the Suzuki reaction, and the catalytic activity decreased with increasing number of imidazole groups. Copyright © 2014 John Wiley & Sons, Ltd.

Catalytic activity of 1-methylimidazole-based phosphine ligands in the palladium-catalyzed Suzuki coupling reaction

An air-stable, copper-free and highly efficient Dppc+PF6−–PdCl2–[bmim][PF6] catalytic system has been developed for the Sonogashira coupling reaction of aryl iodides with various aryl- and alkylacetylenes. The catalytic system allows for facile separation and can be recycled at least eight times with minimal loss of activity. Copyright © 2007 John Wiley & Sons, Ltd.

Dppc+PF6−–PdCl2–[bmim][PF6]–a copper‐free recyclable catalytic system for Sonogashira coupling reaction

A cobaltocene cation diphosphine ligand, its preparing process, and its application in catalytic Suzuki coupling reaction in ionic liquid (the reaction of bromobenzene or substituted bromobenzen on phenylboric acid to generate dibenzene) are disclosed.

Cobait dipenta cation diphosphine ligand preparation and application thereof

Dppc+PF-6-PdCl2-[bmim] [PF6] — A Copper-Free Recyclable Catalytic System for Sonogashira Coupling Reaction.

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Dppc+PF6−–PdCl2–[bmim][PF6]–a copper‐free recyclable catalytic system for Sonogashira coupling reaction

Cobait dipenta cation diphosphine ligand preparation and application thereof

Dppc+PF-6-PdCl2-[bmim] [PF6] — A Copper-Free Recyclable Catalytic System for Sonogashira Coupling Reaction.