Amino acid-mediated Goldberg reactions between amides and aryl iodides

Green alternative solvents for the copper-catalysed arylation of phenols and amides

“…The reaction of benzamide, 4-methoxy benzamide and 3-(trifluoromethyl)benzamide with electron-donating to electronwithdrawing aryl iodides occurred with good yields (25-32, 56% to 91% yields). Arylation of cyclohexanecarboxamide gave products 33-35 with yields between 71% and 78%, while cyclic amides such as 2-pyrrolidinone and 2-hydroxypyridine gave excellent results, with yields of 87-98% (36)(37)(38)(39)(40) [52][53][54] Benzylation also proved effective under these conditions: from the reaction of benzamide with 2-iodobenzyl bromide, a doubly substituted product was obtained in 30% yield (48, Scheme 5), while the coupling with benzyl bromide and benzyl chloride occurred with 52% and 33% yields respectively (49). It is worth noting that product 49 was not observed in reactions without CuI/ligand, either with benzyl bromide or benzyl chloride.…”

Highly efficient copper-catalyzed N-arylation of alkylamines with aryl iodides using phosphoramidite as ligand

“…However, the copper-mediated reaction in mild conditions has become a focus of research for large and industrial-scale production from an economic point of view [8][9][10][11]. Recently, many ligands, such as 1,10-phenanthroline [12][13][14][15][16], trans-1,2-cyclohexadiamine [17][18][19][20][21], ethylene glycol [22,23], amino acid [24,25], and other nitrogen, oxygencontaining ligands [26][27][28][29] have been developed under mild condition in copper-catalyzed aminations. However, only several papers have contributed to N-arylation of alkylamines and just a few ligands were found to be effective in these transformation [30][31][32][33].…”

Understanding the Heteroatom Effect on the Ullmann Copper-Catalyzed Cross-Coupling of X-Arylation (X = NH, O, S) Mechanism

“…These drawbacks were overcome at the beginning of the new century with the introduction of the ancillary chelating ligands (L) approach by the groups of Taillefer [12] and Buchwald [13] representing thus a major breakthrough in copper chemistry. The use of bidentate ligands like phenanthroline [14][15][16][17][18], diamines [19][20][21], amino acids [22][23][24], and 1,3-diketones [25,26] among others [27][28][29][30] has not only met the demands of reliability, mildness, and functional group tolerance but also interesting modern features such as orthogonal reactivity [26]. The applications so far known have been spread over a diverse range of areas from pharmaceutical [31] and natural products [32][33][34] to materials fields [35,36].…”