Copper-facilitated Suzuki-Miyaura coupling for the preparation of 1,3-dioxolane-protected 5-arylthiophene-2-carboxaldehydes

Mechanochemistry through Extrusion: Opportunities for Nanomaterials Design and Catalysis in the Continuous Mode

“…Additionally, the design of recyclable and reusable heterogeneous catalysts can greatly reduce the carbon footprint of the reaction and improve the cost efficiency. Promising results have already been reported with cheap and non-toxic catalysts based on non-endangered metals such as nickel and copper [26][27][28][29][30]. However, Pd-based catalysts continue to be recognized as some of the most popular systems for the Suzuki-Miyaura cross-coupling [31][32][33][34].…”

Application of statistical learning and mechanistic modelling towards mapping the substrate electronic space in a Cu-catalyzed Suzuki–Miyaura coupling

“…32 The Suzuki-Miyaura reaction, one of the most representative metal-catalyzed cross-couplings, has several versions in which the typical palladium catalysts have been replaced by analogous copper complexes. [33][34][35][36][37][38][39] Recently, a Cu-catalyzed Suzuki-Miyaura coupling of highly fluorinated aryl boronate esters with aryl iodides has been reported. 40 This procedure allows preparing polyfluorobiphenyl products that present a wide variety of potential applications in the fields of medicinal chemistry, 41,42 electron-transport materials, 43,44 and supramolecular chemistry.…”

A detailed theoretical investigation to unravel the molecular mechanism of the ligand-free copper-catalyzed Suzuki cross-coupling reaction

“…Since then, several copper-based Suzuki reaction protocols have been reported to facilitate Csp-Csp 2 , Csp 3 -Csp 3 , and Csp 2 -Csp 2 bond formations, including ligand-assisted and ligand-free protocols. [14][15][16][17][18][19][20][21][22][23]25,26,[28][29][30][31][32][33] The term 'ligand-free' refers to the use of metal salts such as MX or MX 2 (M = Cu or Pd and X = halides or acetate) as the pre-catalysts that does not involve any bulky ligands like diamines on the metal. [34][35][36][37] It is well established that the steric effects of bulky ligands such as phosphines or diamines on the metal catalyst could enhance the coupling process by reducing the activation barrier of the reaction.…”