617-89-0Relevant articles and documents
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Reeve,Christian
, p. 860 (1956)
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Selective catalysis for the reductive amination of furfural toward furfurylamine by graphene-co-shelled cobalt nanoparticles
Liu, Jianguo,Ma, Longlong,Zhong, Shurong,Zhuang, Xiuzheng
, p. 271 - 284 (2022/01/19)
Amines with functional groups are widely used in the manufacture of pharmaceuticals, agricultural chemicals, and polymers but most of them are still prepared through petrochemical routes. The sustainable production of amines from renewable resources, such as biomass, is thus necessary. For this reason, we developed an eco-friendly, simplified, and highly effective procedure for the preparation of a non-toxic heterogeneous catalyst based on earth-abundant metals, whose catalytic activity on the reductive amination of furfural or other derivatives (more than 24 examples) proved to be broadly available. More surprisingly, the cobalt-supported catalyst was found to be magnetically recoverable and reusable up to eight times with an excellent catalytic activity; on the other hand, the gram-scale tests catalyzed by the same catalyst exhibited the similar yield of the target products in comparison to its smaller scale, which was comparable to the commercial noble-based catalysts. Further results from a series of analytical technologies involving XRD, XPS, TEM/mapping, and in situ FTIR revealed that the structural features of the catalyst are closely in relation to its catalytic mechanisms. In simple terms, the outer graphitic shell is activated by the electronic interaction as well as the induced charge redistribution, enabling the easy substitution of the –NH2 moiety toward functionalized and structurally diverse molecules, even under very mild industrially viable and scalable conditions. Overall, this newly developed catalyst introduces the synthesis of amines from biomass-derived platforms with satisfactory selectivity and carbon balance, providing cost-effective and sustainable access to the wide applications of reductive amination.
Synthesis of amides and esters containing furan rings under microwave-assisted conditions
Janczewski, ?ukasz,Zieliński, Dariusz,Kolesińska, Beata
, p. 265 - 280 (2021/03/17)
In this work, we present a novel method for the synthesis of ester and amide derivatives containing furan rings (furfural derivatives) under mild synthetic conditions supported by microwave radiation. N-(Furan-2-ylmethyl)furan-2-carboxamide and furan-2-ylmethyl furan-2-carboxylate were produced using 2-furoic acid, furfurylamine, and furfuryl alcohol. The reactions were carried out in a microwave reactor in the presence of effective coupling reagents: DMT/NMM/TsO? or EDC. The reaction time, the solvent, and the amounts of the substrates were optimized. After crystallization or flash chromatography, the final compounds were isolated with good or very good yields. Our method allows for the synthesis of N-blocked amides using N-blocked amino acids (Boc, Cbz, Fmoc) and amine. As well as compounds with a monoamide and ester moiety, products with diamides and diester bonds (N,N-bis(furan-2-ylmethyl) furan-2,5-dicarboxamide, bis(furan-2-ylmethyl) furan-2,5dicarboxylate, and furan-3,4-diylbis(methylene) bis(furan-2-carboxylate)) were synthesized with moderate yields in the presence of DMT/NMM/TsO– or EDC, using 2,5-furan-dicarboxylic acid and 3,4-bis(hydroxymethyl)furan as substrates.
Reductive amination of bio-based 2-hydroxytetrahydropyran to 5-Amino-1-pentanol over nano-Ni-Al2O3catalysts
Zhang, Jia,Yang, Jian,Tian, Junying,Liu, Hailong,Li, Xuemei,Fang, Weiguo,Hu, Xun,Xia, Chungu,Chen, Jing,Huang, Zhiwei
supporting information, p. 4236 - 4245 (2021/03/15)
The synthesis of useful amines from bio-based carbonyl compounds is highly desired owing to their mild reaction conditions and green sustainability. The reductive amination of bio-furfural-derived 2-hydroxytetrahydropyran (2-HTHP) to high-value-added 5-Amino-1-pentanol (5-AP) was carried out over efficient Ni-Al2O3catalysts prepared by a co-precipitation method. Among the Ni-Al2O3catalysts with different Ni loadings (0-100 wt%) tested, the 50Ni-Al2O3catalyst exhibited the highest5-APyield of 91.3% under mild conditions of 60 °C and 2 MPa H2. This catalyst also presented good stability during a 150 h time-on-stream without appreciable deactivation. Characterization results showed that the 50Ni-Al2O3catalyst exhibited small Ni0nanoparticles (5.5 nm), a high reduction degree (up to 95%), and a large amount of strong Lewis acid sites. The cooperative catalysis of the strong Lewis acid sites and highly dispersed metallic Ni sites is suggested to play an important role in achieving high efficiency in2-HTHPreductive amination.