104-86-9Relevant articles and documents
Polarographic and Cyclic Voltametric Reduction of p-Chlorobenzaldehyde Isonicotinoylhydrazone
Reddy, Papammagari Raveendra,Rao, Sukuru Brahmaji
, p. 1397 - 1398 (1988)
p-Chlorobenzaldehyde isonicotinoylhydrazone (p-Cl-BAINH) exhibits a single wave in acid buffered solutions (pH 2-6) and two waves in alkaline buffered solutions (pH 7- 9).However, the compound exhibits three cathodic peaks in acid solution and two cathodic peaks in alkaline solutions.The electrode reactions are attributed to the reductive cleavage of =N-N- linkage and the reduction of the amide formed in the cleavage.
Stable and Inert Cobalt Catalysts for Highly Selective and Practical Hydrogenation of C≡N and C=O Bonds
Chen, Feng,Topf, Christoph,Radnik, J?rg,Kreyenschulte, Carsten,Lund, Henrik,Schneider, Matthias,Surkus, Annette-Enrica,He, Lin,Junge, Kathrin,Beller, Matthias
, p. 8781 - 8788 (2016)
Novel heterogeneous cobalt-based catalysts have been prepared by pyrolysis of cobalt complexes with nitrogen ligands on different inorganic supports. The activity and selectivity of the resulting materials in the hydrogenation of nitriles and carbonyl compounds is strongly influenced by the modification of the support and the nitrogen-containing ligand. The optimal catalyst system ([Co(OAc)2/Phenα-Al2O3]-800 = Cat. E) allows for efficient reduction of both aromatic and aliphatic nitriles including industrially relevant dinitriles to primary amines under mild conditions. The generality and practicability of this system is further demonstrated in the hydrogenation of diverse aliphatic, aromatic, and heterocyclic ketones as well as aldehydes, which are readily reduced to the corresponding alcohols.
Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups
Amberchan, Gabriella,Snelling, Rachel A.,Moya, Enrique,Landi, Madison,Lutz, Kyle,Gatihi, Roxanne,Singaram, Bakthan
supporting information, p. 6207 - 6227 (2021/05/06)
The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.
Comparative account of catalytic activity of Ru- and Ni-based nanocomposites towards reductive amination of biomass derived molecules
Bhanage, Bhalchandra M.,Gokhale, Tejas A.,Raut, Amol B.
, (2021/06/18)
This work includes an effective comparison of metallic ruthenium and nickel nanoparticles loaded on montmorillonite clay (MMT) for reductive amination reaction of biomass-derived molecules. It comprises an eco-friendly reaction using water as a solvent, utilizing molecular hydrogen and liquor ammonia (25% aq. solution) for the synthesis of primary amines from bio-derived aldehydes within 3–10 h of reaction time. Various parameters such as temperature, hydrogen pressure, substrate/ammonia concentration ratio, and reaction time were optimized while comparing the selectivity of primary amines for both catalysts. The applicability scope of these catalysts was explored with a library of aryl and heterocyclic aldehydes. The reductive amination of crude furfural extracted from biomass feedstock (rice husk) and pure xylose sugar was tested, showing yields in the range of 11–36%, to show the wider industrial scope of both nanocomposites. Gram scale conversion was also carried out to showcase the bulk scalability of the Ru/MMT catalyst.
Self-regulated catalysis for the selective synthesis of primary amines from carbonyl compounds
Fan, Xiaomeng,Gao, Jin,Gao, Mingxia,Jia, Xiuquan,Ma, Jiping,Xu, Jie
supporting information, p. 7115 - 7121 (2021/09/28)
Most current processes for the general synthesis of primary amines by reductive amination are performed with enormously excessive amounts of hazardous ammonia. It remains unclear how catalysts should be designed to regulate amination reaction dynamics at a low ammonia-to-substrate ratio for the quantitative synthesis of primary amines from the corresponding carbonyl compounds. Herein we show a facile control of the reaction selectivity in the layered boron nitride supported ruthenium catalyzed reductive amination reaction. Specifically, locating ruthenium to the edge surface of layered boron nitride leads to an increased hydrogenation activity owing to the enhanced interfacial electronic effects between ruthenium and the edge surface of boron nitride. This enables self-accelerated reductive amination reactions which quantitatively synthesize structurally diverse primary amines by reductive amination of carbonyl compounds with twofold ammonia. This journal is