A Simple Method for Preparation of Secondary Aromatic Amines

Reductive amination of aldehydes with sodium borohydride and lithium aluminum hydride in the presence of lithium perchlorate

“…The organic layer was separated, washed with water and dried over MgSO 4 and the solvent was evaporated in vacuo to give the crude product. After purification by short column chromatography or by extraction with 5% HCl solution, all amine compounds were characterized on the basis of their spectroscopic data and by comparison with those reported in the literature [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23]27].…”

“…Many other reagents, such as NaBH 4 /CF 3 COOH [4,5], NaBH 4 /aqueous sulfuric acid [6], borane-pyridine [7], Ti(OiPr) 4 /NaBH 3 CN [8], borohydride exchange resin [9], *Corresponding author. E-mail: saidi@sharif.edu Zn/AcOH [10], NaBH 4 /Mg(ClO 4 ) 2 [11], Zn(BH 4 ) 2 /ZnCl 2 [12], silica gel/Zn(BH 4 ) 2 [13], NiCl 2 /NaBH 4 [14] , Pd/HCOOH [15] and Ti(OiPr) 4 /NaBH 4 [16] for reductive amination of aldehydes and ketones have been reported in the literature. Alternative metal hydride reagents, such as Bu 3 SnH [17], Bu 2 SnClH [18], Bu 2 SnIH [18], Et 3 SiH-trifluoroacetic acid [19], Ti(OiPr) 4 -polymethylhydro-siloxane [20], PhSiH 3 -Bu 2 SnCl 2 [21], -picoline-borane [22], NaBH(OAc) 3 / microwave irradiation [23], dibutylchlorotin hydride complex [24], and electrochemical reductive amination reactions [25] have recently been developed in order to circumvent the drawbacks of the previous reagents.…”

Programmed Synthesis Palladium Supported on Fe3O4@C: An Efficient and Heterogeneous Recyclable Catalyst for One-Pot Reductive Amination of Aldehydes with Nitroarenes in Aqueous Reaction Medium

“…Due to their importance, several methods have been developed for the preparation of amines, such as direct base-promoted N-alkylation and direct reductive amination [3,4]. However, it's still a challenge to control the monoalkylation of primary amines [5], the synthesis of a wide variety of substituted amines relies heavily on the reductive amination of the carbonyl compounds [6,7], but the method is usually carried out with hydride-based reagents such as NaBH 4 [8], pyridine-BH 3 [9], Zn-AcOH [10], Et 3 SiH-CF 3 CO 2 H [11], Bu 3 SnHDMF [12], InCl 3 -Et 3 SiH [13], and various modified borohydride derivatives [14]. These reagents have certain limitations such as the dependence of a stoichiometric amount of reductant, poor functional group tolerance, side reactions, overalkylation, toxic waste, thermal instability, handling risks, and rigorous reaction conditions [15].…”

Practical One-Pot Synthesis of Secondary Amines by Zinc-Catalyzed Reductive Amination

“…Here the use of zinc is probably of great interest [37][38][39][40][41][42][43][44][45][46][47][48][49]. Although several research groups demonstrated the abilities of zinc catalysts in the reduction of imines [50][51][52][53], reductive amination protocols are scarcely reported [54][55][56][57][58][59][60]. In most cases stoichiometric or sub-stoichiometric amounts of zinc reagents or special reducing reagents were applied.…”