111-26-2Relevant articles and documents
Hydrogenation Properties of Nanostructured Tungsten Carbide Catalysts in a Continuous-Flow Reactor
Braun, Max,Esposito, Davide
, p. 393 - 397 (2017)
Tungsten monocarbide (WC) obtained through a urea glass route showed a high activity and chemoselectivity for the continuous-flow reduction of a variety of nitro compounds under milder conditions than those reported previously. The favorable effect of the nanostructure was shown by comparison with other commercially available WC materials. Moreover, WC functioned as an efficient support for Ni nanoparticles. This expanded its range of applicability and led to a bimetallic Ni@WC composite characterized by a high activity for the hydrogenation of cardanol, a phenolic lipid obtained from cashew nut shells.
Nanopalladium on amino-functionalized mesocellular foam as an efficient and recyclable catalyst for the selective transfer hydrogenation of nitroarenes to anilines
Verho, Oscar,Nagendiran, Anuja,Tai, Cheuk-Wai,Johnston, Eric V.,Baeckvall, Jan-E.
, p. 205 - 211 (2014)
Herein, we report on the use of nanopalladium on amino-functionalized siliceous mesocellular foam as an efficient heterogeneous catalyst for the transfer hydrogenation of nitroarenes to anilines. In all cases, the protocol proved to be highly selective and favored the formation of the desired aniline as the single product in high yields with short reaction times if naturally occurring and renewable γ-terpinene was employed as the hydrogen donor. Furthermore, the catalyst displayed excellent recyclability over five cycles and negligible leaching of metal into solution, which makes it an eco-friendly and economic catalyst to perform this transformation. The scalability of the protocol was demonstrated with the reduction of 4-nitroanisole on a 2 g scale, in which p-anisidine was isolated in 98 % yield. Copyright
N-doped carbon supported Pd catalysts for N-formylation of amines with CO2/H2
Luo, Xiaoying,Zhang, Hongye,Ke, Zhengang,Wu, Cailing,Guo, Shien,Wu, Yunyan,Yu, Bo,Liu, Zhimin
, p. 725 - 731 (2018)
Using mesoporous N-doped carbons (NCs) derived from glucose and melamine as the supports, a series of Pd/NC catalysts were prepared, in which Pd nanoparticles with average size2 and H2 in ethanol without any additives. Especially, the catalyst Pd/NC-800-6.9% containing quaternary N showed the best performance, affording a series of formylamides in good or even excellent yields. Further investigation reveals that the interaction between the Pd nanoparticles and quaternary nitrogen in the NC support was responsible for the good performance of the catalyst.
Fe3O4 nanoparticles: A conveniently reusable catalyst for the reduction of nitroarenes using hydrazine hydrate
Kim, Seyoung,Kim, Eunsuk,Kim, B. Moon
, p. 1921 - 1925 (2011)
A magnetic personality: Commercially available Fe3O4 nanoparticles were utilized for efficient nitroarene reductions, and could be recycled up to 10 times using magnetic separation, whilst retaining activity (99 % aniline yield in each case without any side-products). Excellent chemoselectivity for reduction of the nitro versus other functional groups, such as halogen, ester, O-benzyl, and N-Cbz groups, was observed.
The chemistry of N,N-bis(trialkylsilyloxy)enamines 2. Alkylation of primary amines with N,N-bis(trimethylsilyloxy)enamines
Makarenkova,Bliznets,Ioffe,Strelenko,Tartakovsky
, p. 1261 - 1269 (2000)
The reactions of primary amines with N,N-bis(trimethylsilyloxy)enamines can give products of both mono- and bis-α-oximinoalkylation of primary amines. The steric restrictions in both reactants substantially retard bis-α-oximinoalkylation. A general method for the synthesis of α-amino-substituted oximes from primary amines and bis-silyl derivatives of aliphatic nitro compounds was developed.
PHOTODETOSYLATION OF SULFONAMIDES INITIATED BY ELECTRON TRANSFER FROM AN ANIONIC SENSITIZER
Art, J. F.,Kestemont, J. P.,Soumillion, J. Ph.
, p. 1425 - 1428 (1991)
A new and efficient photosensitized process for the detosylation of a wide variety of sulfonamides is presented.The excited β-naphthoxide anion is used as sensitizer, in methanol as solvent.Electron transfer from the excited naphthoxide anion to the electron-accepting sulfonamide leads, in the presence of sodium borohydride, to the recovering of amines after cleavage of the radical anion.
A biocatalytic cascade for the conversion of fatty acids to fatty amines
Citoler, Joan,Derrington, Sasha R.,Galman, James L.,Bevinakatti, Han,Turner, Nicholas J.
, p. 4932 - 4935 (2019)
Fatty amine synthesis from renewable sources is an energetically-demanding process involving toxic metal catalysts and harsh reaction conditions as well as selectivity problems. Herein we present a mild, biocatalytic alternative to the conventional amination of fatty acids through a one-pot tandem cascade performed by a carboxylic acid reductase (CAR) and a transaminase (ω-TA). Saturated and unsaturated fatty acids, with carbon chain lengths ranging from C6 to C18, were successfully aminated obtaining conversions of up to 96%.
Depolymerization of Technical-Grade Polyamide 66 and Polyurethane Materials through Hydrogenation
Zhou, Wei,Neumann, Paul,Al Batal, Mona,Rominger, Frank,Hashmi, A. Stephen K.,Schaub, Thomas
, p. 4176 - 4180 (2021)
Chemical recycling provides a promising solution to utilize plastic waste. Here, a catalytic hydrogenative depolymerization of polyamide 66 (PA 66) and polyurethane (PU) was developed. The system employed Ru pincer complexes at high temperature (200 °C) in THF solution, and even technical-grade polymers could be hydrogenated with satisfactory yields under these conditions. A comparison of the system with some known heterogeneous catalysts as well as catalyst poisoning tests supported the homogeneity of the system. These results demonstrate the potential of chemical recycling to regain building blocks for polymers and will be interesting for the further development of polymer hydrogenation.
Elucidation of reaction scheme describing malondialdehyde - Acetaldehyde - Protein adduct formation
Tuma,Kearley,Thiele,Worrall,Haver,Klassen,Sorrell
, p. 822 - 832 (2001)
Malondialdehyde and acetaldehyde react together with proteins and form hybrid protein conjugates designated as MAA adducts, which have been detected in livers of ethanol-fed animals. Our previous studies have shown that MAA adducts are comprised of two distinct products. One adduct is composed of two molecules of malondialdehyde and one molecule of acetaldehyde and was identified as the 4-methyl-1,4-dihydropyridine-3,5-dicarbaldehyde derivative of an amino group (MDHDC adduct). The other adduct is a 1:1 adduct of malondialdehyde and acetaldehyde and was identified as the 2-formyl-3-(alkylamino)butanal derivative of an amino group (FAAB adduct). In this study, information on the mechanism of MAA adduct formation was obtained, focusing on whether the FAAB adduct serves as a precursor for the MDHDC adduct. Upon the basis of chemical analysis and NMR spectroscopy, two initial reaction steps appear to be a prerequisite for MDHDC formation. One step involves the reaction of one molecule of malondialdehyde and one of acetaldehyde with an amino group of a protein to form the FAAB product, while the other step involves the generation of a malondialdehyde - enamine. It appears that generation of the MDHDC adduct requires the FAAB moiety to be transferred to the nitrogen of the MDA - enamine. For efficient reaction of FAAB with the enamine to take place, additional experiments indicated that these two intermediates likely must be in positions on the protein of close proximity to each other. Further studies showed that the incubation of liver proteins from ethanol-fed rats with MDA resulted in a marked generation of MDHDC adducts, indicating the presence of a pool of FAAB adducts in the liver of ethanol-fed animals. Overall, these findings show that MDHDC - protein adduct formation occurs via the reaction of the FAAB moiety with a malondialdehyde - enamine, and further suggest that a similar mechanism may be operative in vivo in the liver during prolonged ethanol consumption.
REDUCTION D'AZIDES EN AMINES PAR LE FORMIATE D'AMMONIUM PAR "TRANSFERT D'HYDROGENE CATALYSE" (CTH)
Gartiser, T.,Selve, C.,Delpuech, J.-J.
, p. 1609 - 1610 (1983)
The azides are reduced to amines in very good yields by "Catalytic Transfer Hydrogenation" (CTH) using ammonium formate.
