22643-14-7Relevant articles and documents
Highly Selective Reductive Cross-Amination between Aniline or Nitroarene Derivatives and Alkylamines Catalyzed by Polysilane-Immobilized Rh/Pt Bimetallic Nanoparticles
Suzuki, Aya,Miyamura, Hiroyuki,Kobayashi, Shu
, p. 387 - 392 (2019)
Reductive cross-amination between imine intermediates generated through partial hydrogenation of aniline or nitroarene derivatives and alkylamines is an ideal method for obtaining N-alkylated cyclohexylamine derivatives; however, no such transformations have hitherto been established. Here, we report a highly selective reductive cross-amination using aniline derivatives and alkylamines catalyzed by heterogeneous Rh/Pt bimetallic nanoparticles under mild conditions. The catalyst was recovered and reused for five runs, keeping high activity. In this reaction, imine intermediates generated during the course of partial hydrogenation of aniline derivatives were trapped immediately by strongly interacting primary alkylamines with the catalyst, which caused a highly selective transformation to give the desired products, while suppressing dicyclohexylamine formation.
Ni-Catalyzed reductive amination of phenols with ammonia or amines into cyclohexylamines
Cuypers, Thomas,Morias, Thomas,Windels, Simon,Marquez, Carlos,Van Goethem, Cédric,Vankelecom, Ivo,De Vos, Dirk E.
, p. 1884 - 1893 (2020/04/07)
Phenol and its derivatives, which naturally occur in lignocellulose, can be considered as a renewable feedstock not only for aromatic, but also for alicyclic compounds, such as primary and N-substituted cyclohexylamines. So far, the latter are mostly produced from non-renewable starting materials like benzene via problematic nitration/reduction or cross-coupling routes. Herein, an efficient reductive amination of phenol with ammonia or amines is demonstrated, for the first time without the need for rare and expensive noble metals and without using any additives. Various supported Ni catalysts were screened and we elucidated the influence of the key parameters, including the acid-base properties of the supporting material. Acquired knowledge was then applied to different phenol-ammonia/amine combinations, resulting in the synthesis of various primary, secondary and tertiary cyclohexylamines in fair to very high yields.
Synthesis method for converting lignin 4-O-5 model compound diaryl ether into nitrogen-containing compound
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Paragraph 0045-0047, (2019/04/26)
The invention discloses a synthesis method for converting lignin 4-O-5 model compound diaryl ether into a nitrogen-containing compound. According to the synthesis method, a diaryl ether compound andan amine compound are subjected to a heating reaction in a certain amount of a solvent (containing a certain amount of water) in an argon atmosphere (containing a certain amount of air) under the actions of a metal catalyst and sodium borohydride, such that the drug with the important physiological activity or the compound with the natural product skeleton containing nitrogen is formed by directlycoupling the C-O bond cut and the amine compound cross while the corresponding aromatic hydrocarbon is obtained. According to the present invention, the synthesis method has characteristics of simpleand easily-available raw materials, high conversion rate, important product and good yield, and has broad application prospects in the degradation and deep development and utilization of lignin.
