Reductive Amination of Furanic Aldehydes in Aqueous Solution over Versatile Ni_yAlO_x Catalysts

Abstract

We disclose in this study a Ni 6 AlO x catalyst prepared by coprecipitation for the reductive amination of biomass-derived aldehydes and ketones in aqueous ammonia under mild reaction conditions. The catalyst exhibited 99% yield toward 5-aminomethyl-2-furylmethanol in the reaction of 5-hydroxymethyl furfural with ammonia at 100 °C for 6 h under 1 bar H 2 . The catalyst was further extended to the reductive amination of a library of aromatic and aliphatic aldehydes and ketones with a yield in the range 81–90% at optimized reaction conditions. Besides, 5-hydroxymethylfurfural could react with a library of primary and secondary amines with yields in the range 76–88%. The catalyst could be easily recycled and reused without apparent loss of activity in four consecutive runs.

Sustainable access to renewable N-containing chemicals from reductive amination of biomass-derived platform compounds

“…Recently, the combination of carbon monoxide and water has proven capable of serving as a good reducing agent for hydrogenation reactions in organic chemistry [105,106]. [99] and Co-DABCO-TPA@C-800 [100]) also exhibited remarkable performance for the reductive amination of HMF with gaseous ammonia to exclusively produce 5-aminomethyl-2-furylmethanol (yields of 99% and 89%) under mild conditions (T ≤ 120 °C). Thus, it seems that the reactivity of HMF in the reductive amination with gaseous ammonia is superior to furfural in terms of target product yield and reaction conditions.…”

Effective synthesis of 5-amino-1-pentanol by reductive amination of biomass-derived 2-hydroxytetrahydropyran over supported Ni catalysts

“…These processes generally suffer from high cost due to the lack of organic feedstocks with special functional group(s) or the generation of large amounts of waste. Therefore, much attention has been paid to the development of new catalytic processes for the efficient and sustainable production of primary amines [2,[4][5][6][7][8][9].…”

Homogeneous Catalyzed Valorization of Furanics: A Sustainable Bridge to Fuels and Chemicals

“…Those chemicals can be produced via different processes. For example, the typical reactions that the furanic aldehyde functionality can undergo are reduction to alcohols by H 2 or by hydrogen transfer (Meerwein-Ponndorf-Verley reduction) [47], decarbonylation [48], reductive amination to amines [49], oxidation to carboxylic acid [50], acetalization [51], aldol and Knoevenagel condensations [52], acylation, and Grignard reactions [53]. The second reactive functionality is the hydroxyl group that can undergo hydrogenolysis of the C−O bond, oxidation to an aldehyde or acid, etherification, acetalization, esterification, and halogenation reactions [54].…”