Direct and indirect reductive amination of aldehydes and ketones with solid acid-activated sodium borohydride under solvent-free conditions

One-Pot Reductive Amination of Carbonyl Compounds Using Sodium Borohydride-Cellulose Sulfuric Acid

“…13 the most often used reagents for this purpose ( Table 1, entry 8 and 12). However, in order to examine a wider range of amines and to better illustrate the scope and limitation of this method, we investigated the reaction with both primary and secondary amines such as benzylamine, piperidine, pyrrolidine and morpholine using PhCHO as a representative aldehyde, and cyclohexanone as a representative ketone (Table 1, entries [13][14][15][16][18][19][20]. Reductive amination of aliphatic aldehyde, such as butanal with aniline also gives excellent yield of corresponding amine (Table 1, entry 23).…”

“…2 A variety of reducing agents, such as hydrogen in the presence of metal catalysts, 3 NaBH3CN, 4 NaBH(OAC)3, 5 silica gel-Zn(BH4)2, 6 Ti(O-i-Pr)4-NaBH4, 7 NaBH4-H2SO4, 8 NaBH4-ZrCl 4 , 9 NaBH 4 -NiCl 2 , 10 NaBH 4 -wet-clay-microwave, 11 pyridine-BH3, 12 NaBH4-H3BO3, 13 Zr[(BH4)2(Cl)2(dabco)2], 14 Et3-SiH-CF3CO2H, 15 NaBH4 in micellar media, 16 zinc borohydride N-methyl piperidine, 17 NaBH4-H3PW12O40, 18 NaBH4-Silica phosphoric acid, 19 zinc borohydride N-methyl pyrrolidine 20 NaBH4-Silica-Gel-supported sulfuric acid, 21 NaBH4-Amberlyst 15 22 and NaBH 4 -silica chloride 23 have been developed. However, most of these methods suffer from one or more drawbacks.…”

Cleaner and Efficient Green Chemistry Synthesis of N,N´-Dibenzyl or N,N´-(2-Hydroxybenzyl)-Ethane-1,2-Diamine,-Propane-1,3-Diamine and -1,3-Diamino-2-Propanol

“…Indeed, in many cases, solid-state organic reactions occur more efficiently and more selectively than do their counterparts in solution; furthermore, solvent-free reactions have many advantages: reduced pollution, low cost, and simple processing and handling (Tanaka & Toda, 2000). In recent years, environmentally benign synthetic methods have received significant attention and some solvent-free protocols for imine reduction have been reported (Mohammadi & Setamdideh, 2015;Hasanloie & Setamdideh, 2014;Setamdideh & Sepehraddin, 2014;Alinezhad & Tollabian, 2010;Alinezhad, Tajbakhsh & Mahdavi, 2010;Cho & Kung, 2005). In this work we report an alternative, simple solvent-free procedure for the synthesis of tetrahydro-di-Schiff bases that uses sodium borohydride as a reducing agent.…”

NaBH4/C: A Convenient System for Reductive Amination of Aldehydes

“…Because, other approaches such as: the reduction of nitro, cyano, azide, carboxamide compounds or the alkylation of amines are often problemssuch as: harsh reaction conditions, overalkylation, low chemical selectivity and generally poor yields. The reductive aminationreactionhas been carried out by sodium borohydridewith different reducing system [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] .But, in continuing our efforts for the development of new reducing systems [16][17][18][19][20][21][22][23][24][25][26][27][28] ,in this context, we have reported the reductive amination reaction of aldehydes with anilines by NaBH 4 /C system in THF.…”