Reductive amination of oxygen-containing organic compounds

Liquid-phase hydroamination of cyclohexanone

“…This result agrees with the previous studies, which showed that pri mary amines were the major products of hydroamination of carbonyl compounds in the presence of the nickel con taining catalysts. 4,7 The data on the catalyst activity at a moderate conver sion of cyclohexanone are listed in Table 3. The moderate cyclohexanone conversion is achieved due to a decrease in the amount of the catalyst used (0.01 g) and the reac tion time (1 h).…”

“…4,7,10, 11 The nick el catalysts are considered to be most available and effi cient for cyclohexylamine production. 4,7 According to the commonly accepted mechanism of ketone hydroamination, 2,4,7,8,12,13 at the first non cata lytic step ammonia reacts with ketone to form intermedi ate primary imine, which is further hydrogenated on the catalyst to form primary amine. In turn, the primary amine can react with ketone to form secondary imine, whose hydrogenation gives secondary amine.…”

“…[1][2][3][4] Carbonyl compounds are hydroaminated by ammonia and hydrogen in the presence of hydrogenation catalysts, among which the catalysts based on nickel and platinum group metals are used most frequently. 4 This reaction was first carried out in the liquid phase at room temperature and atmospheric pressure on the nickel and copper cata lysts. 5 Higher yields of amines were obtained by using Raney nickel at elevated hydrogen pressure (20-150 atm) and 40-150 °С (see Ref.…”

Asymmetric Hydroamination and Reductive Amination in Total Synthesis

“…[93][94][95][96][97] There are a large number of reports available in the literature that deal with the asymmetric imine reduction, 98 but there are few reports available on asymmetric reductive amination. 99 is an N-chloroacetylated, N-alkoxyalkylated orthodisubstituted aniline that works excellently as grass herbicides by controlling certain broadleaf weed species and annual grassy weeds.…”

Recent contributions to the Diversity-Oriented Synthesis (DOS) mediated by iminium ions through multicomponent Mannich-type reactions

“…step (ii)). The reduction process of ketones 30 was efficiently performed by two different approaches: (a) by a catalytic hydrogenation on a Parr apparatus in the presence of Nickel-Raney as catalyst, methanol as solvent at room temperature, 58,59 and (b) by a chemical reduction with NaBH 4 in methanol at room temperature to afford the expected γ-aminoalcohols 31 in (72-93%) or (57-96%) isolated yields, respectively, Table 3. 55 Table 3. Synthesis of the novel β-aminoketones 30{1,1} through 30{22,2} and γ-aminoalcohols 31{1,1} through 31{22,2} 55 a Values in parentheses correspond to the isolated yields of alcohols obtained by catalytic hydrogenation.…”