Recent advances and perspectives in copper-catalyzed Sonogashira coupling reactions

Abstract

The review highlights the origin, development, mechanistic insights and recent applications of Cu-catalyzed Sonogashira coupling reactions.

Copper-Mediated Intermolecular C–H/C–H and C–H/N–H Couplings via Aromatic C–H Cleavage

“…A powerful and reliable approach to these molecules is the palladium/copper-catalyzed cross-coupling of aryl halides with terminal alkynes, also known as the Sonogashira coupling [13][14][15][16]. However, the stoichiometric halogenation of arenes is inevitable for the preparation of the starting halogenated arenes.…”

Synthesis and reactivity of imidazole-1-sulfonate esters (imidazylates) in substitution, elimination, and metal-catalyzed cross-coupling reactions: a review

“…[45] This reaction has many desirable features like mild technically simple high yield reaction conditions and high efficiency, and is tolerant toward a wide variety of functional groups. [63,64] Traditionally, palladium or palladium/copper is an excellent catalyst for C(sp 2 )-C(sp) Sonogashira coupling reactions. However, in recent years numerous other metals have been shown to be effective catalysts for this reaction.…”

“…[59][60][61][62][63] The resulting products are highly valued in natural product and materials synthesis and in the pharmaceutical industry. [45] This reaction has many desirable features like mild technically simple high yield reaction conditions and high efficiency, and is tolerant toward a wide variety of functional groups.…”

Preparation of Multivalent Carbohydrate Mimetics Based on Enantiopure 1,2‐Oxazines by Sonogashira Coupling and Subsequent Reductive Ring‐Opening

“…These impressive results were obtained by the multivalent [8] presentation of sulfated pyran moieties (ca. Owing to the mild reaction conditions, high efficacy, and good functional group tolerance, [10] Sonogashira coupling reactions are frequently used for the construction of multivalent systems from ligands and suitable scaffolds, [11] and as well for the construction of multivalent glycoconjugates. [9] These sialyl Lewis X ana-logues can be considered as potential drug candidates for chronic inflammations such as asthma.…”