Chemoselective Chan-Lam coupling by directly using copper powders via mechanochemical metal activation for catalysis

Recent advances in Chan–Lam coupling reaction

“…Wu and research team demonstrated mechanochemical metal activation for catalysis via ball-milling, which enabled the highly chemo-selective Chan–Lam coupling of (benz)imidazoles, anilines, and alkyl amines by directly using a catalytic amount of commercial copper powder in methanol. 39 With 10 mol% copper powder in MeOH, the N -arylation of benzimidazole with PhB(OH) 2 yielded the desired products in good yield (Scheme 30). Electron-deficient benzimidazoles reacted more slowly than neutral ones, while 5-nitrobenzimidazole underwent no reaction.…”

Mechanoredox/Nickel Co-Catalyzed Cross Electrophile Coupling of Benzotriazinones with Alkyl (Pseudo)halides

“…In fact, beyond the solvent-free privilege, mechanochemistry has shown a couple of features, in particular, in metal-involved processes, including clean activation of metal surfaces, good compatibility with air and moisture, circumvention of solubility limitation, enhanced mixing of solid materials, and even realization of unusual selectivities and/or reactivities . For example, mechanochemical metal activation has been successfully applied in the Reformatsky reaction, Grignard reaction, Pd-catalyzed Negishi coupling, Ni-catalyzed cross electrophile coupling between aryl/alkyl halides, Cu-catalyzed Chan–Lam C–N coupling, and Li or Mn-based reduction reaction . More recently, Kubota and Ito have seminally proposed mechanoredox by harvesting mechanical energy through piezoelectricity as a ground-breaking technique to initiate single electron transfer (SET) for redox processes, leading to the emerging mechanoredox catalysis with highly potential applications in a diversity of fields such as organic syntheses, polymerization, ,, renewable energy production, ,,, and environmental remediation. ,,, …”

Copper Complexes with N,N,N-Tridentate Quinolinyl Anilido-Imine Ligands: Synthesis and Their Catalytic Application in Chan−Lam Reactions

“…In 1998, this name reaction was first reported to construct C-X bonds through the coupling between arylboronic acids and different nucleophiles in the presence of Cu(OAc) 2 as a catalyst (Scheme 1a) [7][8][9]. Since then, Cu and other transition metal-catalyzed Chan-Lam reactions have contributed greatly to C-N bond formation [10][11][12][13].…”