100-46-9Relevant articles and documents
Preparation and characterization of primary amines by potassium borohydride-copper chloride system from nitriles
Jiang, Han,Hu, Jialei,Xu, Xinliang,Zhou, Yifeng
, p. 3564 - 3566 (2015)
Nitriles undergo reduction to primary amines under optimized conditions at 50 °C using 0.25 equiv of copper chloride and 3.0 equiv of potassium borohydride in 80 % isopropanol. The aromatic and aralkyl nitriles could be effectively reduced in yield ranging from 60 to 90 %.
Catalytic transamidation under moderate conditions
Eldred, Sarah E.,Stone, David A.,Gellman, Samuel H.,Stahl, Shannon S.
, p. 3422 - 3423 (2003)
The carboxamide group is generally inert, except under harsh conditions or in the presence of highly evolved enzymes. We have identified several metal complexes that efficiently catalyze transamidation reactions of amide/amine mixtures under moderate cond
Electronic Effect of Ruthenium Nanoparticles on Efficient Reductive Amination of Carbonyl Compounds
Komanoya, Tasuku,Kinemura, Takashi,Kita, Yusuke,Kamata, Keigo,Hara, Michikazu
, p. 11493 - 11499 (2017)
Highly selective synthesis of primary amines over heterogeneous catalysts is still a challenge for the chemical industry. Ruthenium nanoparticles supported on Nb2O5 act as a highly selective and reusable heterogeneous catalyst for the low-temperature reductive amination of various carbonyl compounds that contain reduction-sensitive functional groups such as heterocycles and halogens with NH3 and H2 and prevent the formation of secondary amines and undesired hydrogenated byproducts. The selective catalysis of these materials is likely attributable to the weak electron-donating capability of Ru particles on the Nb2O5 surface. The combination of this catalyst and homogeneous Ru systems was used to synthesize 2,5-bis(aminomethyl)furan, a monomer for aramid production, from 5-(hydroxymethyl)furfural without a complex mixture of imine byproducts.
A Mild and Base-Free Protocol for the Ruthenium-Catalyzed Hydrogenation of Aliphatic and Aromatic Nitriles with Tridentate Phosphine Ligands
Adam, Rosa,Bheeter, Charles Beromeo,Jackstell, Ralf,Beller, Matthias
, p. 1329 - 1334 (2016)
A novel protocol for the general hydrogenation of nitriles in the absence of basic additives is described. The system is based on the combination of [Ru(cod)(methylallyl)2] (cod=cyclooctadiene) and L2. A variety of aromatic and aliphatic nitriles is hydrogenated under mild conditions (50 °C and 15 bar H2) with this system. Kinetic studies revealed higher activity in the case of aromatic nitriles compared with aliphatic ones.
β-TRIMETHYLSILYLETHANESULFONYL CHLORIDE (SES-Cl): A NEW REAGENT FOR PROTECTION OF AMINES
Weinreb, Steven M.,Demko, Donald M.,Lessen, Thomas A.,Demers, James P.
, p. 2099 - 2102 (1986)
The title compound, easily prepared in two steps from vinyltrimethylsilane, is a useful reagent for the protection of primary and secondary amines as their sulfonamides, which are cleaved by fluoride ion.
Total synthesis of capsaicin analogues from lignin-derived compounds by combined heterogeneous metal, organocatalytic and enzymatic cascades in one pot
Anderson, Mattias,Afewerki, Samson,Berglund, Per,Cordova, Armando
, p. 2113 - 2118 (2014)
The total synthesis of capsaicin analogues was performed in one pot, starting from compounds that can be derived from lignin. Heterogeneous palladium nanoparticles were used to oxidise alcohols to aldehydes, which were further converted to amines by an enzyme cascade system, including an amine transaminase. It was shown that the palladium catalyst and the enzyme cascade system could be successfully combined in the same pot for conversion of alcohols to amines without any purification of intermediates. The intermediate vanillylamine, prepared with the enzyme cascade system, could be further converted to capsaicin analogues without any purification using either fatty acids and a lipase, or Schotten-Baumann conditions, in the same pot. An aldol compound (a simple lignin model) could also be used as starting material for the synthesis of capsaicin analogues. Using L-alanine as organocatalyst, vanillin could be obtained by a retro-aldol reaction. This could be combined with the enzyme cascade system to convert the aldol compound to vanillylamine in a one-step one-pot reaction.
Ruthenium(II)-cored supramolecular organic framework-mediated recyclable visible light photoreduction of azides to amines and cascade formation of lactams
Wu, Yi-Peng,Yan, Meng,Gao, Zhong-Zheng,Hou, Jun-Li,Wang, Hui,Zhang, Dan-Wei,Zhang, Junliang,Li, Zhan-Ting
, p. 1383 - 1386 (2019)
Ru(bpy)3]2+-cored supramolecular organic framework SMOF-1, assembled from a [Ru(bpy)3]2+-derived hexaarmed molecule and cucurbit[8]uril, has been demonstrated to heterogeneously catalyze visible light-induced reduction of phenyl, benzyl, 2-phenylethyl and 3-phenylpropyl azides in acetonitrile to produce the corresponding amines in good to high yields. For the last two kinds of azides that bear a CO2Me group at the para-position of the benzene ring, cascade reactions take place to generate the corresponding lactams in high yields. Compared with homogeneous control [Ru(bpy)3]Cl2, SMOF-1 exhibits remarkably increased photocatalysis activity as a result of synergistic effect of the [Ru(bpy)3]2+ units that form cubic cages to host the azide molecules and related intermediates. Moreover, SMOF-1 displays high recyclability and considerable photocatalysis activity after 3 to 12 runs.
Tandem dehydrogenation of ammonia borane and hydrogenation of nitro/nitrile compounds catalyzed by graphene-supported NiPd alloy nanoparticles
Goeksu, Haydar,Ho, Sally Fae,Metin, Oender,Korkmaz, Katip,Mendoza Garcia, Adriana,Gueltekin, Mehmet Serdar,Sun, Shouheng
, p. 1777 - 1782 (2014)
We report a facile synthesis of monodisperse NiPd alloy nanoparticles (NPs) and their assembly on graphene (G) to catalyze the tandem dehydrogenation of ammonia borane (AB) and hydrogenation of R-NO2 and/or R-CN to R-NH2 in aqueous methanol solutions at room temperature. The 3.4 nm NiPd alloy NPs were prepared by coreduction of nickel(II) acetate and palladium(II) acetlyacetonate by borane-tert-butylamine in oleylamine and deposition on G via a solution phase self-assembly process. G-NiPd showed composition-dependent catalysis on the tandem reaction with G-Ni 30Pd70 being the most active. A variety of R-NO 2 and/or R-CN derivatives were reduced selectively into R-NH 2 via G-Ni30Pd70 catalyzed tandem reaction in 5-30 min reaction time with the conversion yields reaching up to 100%. Our study demonstrates a new approach to G-NiPd-catalyzed dehydrogenation of AB and hydrogenation of R-NO2 and R-CN. The G-NiPd NP catalyst is efficient and reusable, and the reaction can be performed in an environment-friendly process with short reaction times and high yields.
Reductive amination of furfural to furfurylamine using aqueous ammonia solution and molecular hydrogen: An environmentally friendly approach
Chatterjee, Maya,Ishizaka, Takayuki,Kawanami, Hajime
, p. 487 - 496 (2016)
A simple and highly efficient method was developed for the transformation of furfural (a biomass derived aldehyde) to furfurylamine by reductive amination using an aqueous solution of ammonia and molecular hydrogen as an amine source and a reducing agent, respectively. By choosing a suitable catalyst, such as Rh/Al2O3, and reaction conditions, a very high selectivity of furfurylamine (～92%) can be achieved within the reaction time of 2 h at 80 °C. A detailed analysis of the reaction system sheds some light on the reaction pathway and provides an understanding about each elementary step. The reaction was believed to proceed via an imine pathway although no such intermediate was detected because of the highly reactive nature. Optimization of different reaction parameters such as hydrogen pressure, temperature and substrate/ammonia mole ratio is shown to be critical to achieve high selectivity of furfurylamine. Time-dependent reaction profiles suggested that a Schiff base type intermediate was in the detectable range, which offers indirect evidence of the formation of imine. Competitive hydrogenation and amination of an aldehyde group were strongly dictated by the nature of the metal used. The studied protocol represents an environmentally benign process for amine synthesis, which can be effectively extended to the other aldehydes also. The studied catalyst could be recycled successfully without any significant loss of catalytic activity.
A Pd/CeO2 “H2 Pump” for the Direct Amination of Alcohols
Yan, Zhen,Tomer, Ajay,Perrussel, Gaetan,Ousmane, Mohamad,Katryniok, Benjamin,Dumeignil, Franck,Ponchel, Anne,Liebens, Armin,Pera-Titus, Marc
, p. 3347 - 3352 (2016)
A Pd/CeO2 catalyst with a prominent reversible H2 storage capacity revealed a high activity and selectivity in the direct amination of benzyl alcohol with aniline and ammonia via the borrowing hydrogen mechanism.
