Natural alkaloids for copper-catalyzed N-arylation of amines and nitrogen-containing heterocycles

Recent advances in Sonogashira reactions

“…306 Also, copper(II) acetate (15 mol%) is able to act as catalyst in the cross-coupling of 4-iodoanisole and phenylacetylene when combined with (À)-sparteine (30 mol%), using potassium carbonate as base in DMF or DMSO as solvent at 130 1C. 307 Some copper complexes have been used in Sonogashira reactions. Thus, the copper(II) complex [Cu(DMEDA) 2 ]Cl 2 ÁH 2 O (0.5 or 0.05 mol%) (DMEDA = N,N 0 -dimethylethylenediamine) has been employed to catalyse the coupling of aryl iodides with aryl alkynes, the reaction being carried out in the presence of a large excess of the ligand DMEDA (30 mol%), caesium carbonate as base in dioxane at 135 1C.…”

A decennary update on applications of metal nanoparticles (MNPs) in the synthesis of nitrogen- and oxygen-containing heterocyclic scaffolds

“…The authors claimed that the use of a magnetic ltration pad allows easier separation, which can be recycled without loss in its catalytic activity. 467 The authors also compared the catalytic efficiency of the previously reported protocols catalyzed by CuFAP, 92 silica-immobilized Cu complexes, 460 cellulose-supported Cu(0), 468 polyanilinesupported CuI, 112 Cu(II)-NaY zeolite, 95 Cu 2 O, 109 nano-CuO, 110 metformin/CuI complex, 469 bis(m-iodo)bis((À)-sparteine)dicopper(I) [Cu 2 I 2 ((À)-sparteine) 2 ], 470 Cu(OAc) 2 H 2 O/8-hydroxyquinoline 471 and CuI with ligand magnetic nanoparticle-supported proline (MNP-3) 99 for the N-arylation of imidazoles with iodobenzene with their developed protocols and claimed that the Fe 3 O 4 @SiO 2 -dendrimer-encapsulated Cu(II) catalyst is superior since it can complete the reaction within 4 h with 96% yield of N-phenyl imidazole.…”

Cross‐Coupling Reactions to sp Carbon Atoms

“…It has also been demonstrated that simple Cu(acac) 2 (acac, acetylacetonate) can be used to catalyze the coupling of 4-iodoanisole and phenylacetylene when combined with (−)-sparteine and K 2 CO 3 in DMF or DMSO at 130 • C [150]. The phosphine ligands have often been replaced by amine-based ligands in Cu-catalyzed coupling reactions.…”