918666-97-4Relevant articles and documents
Selective hydrodeoxygenation of acetophenone derivatives using a Fe25Ru75@SILP catalyst: a practical approach to the synthesis of alkyl phenols and anilines
Bordet, Alexis,Goclik, Lisa,Leitner, Walter,Walschus, Henrik
supporting information, p. 2937 - 2945 (2022/04/07)
A versatile synthetic pathway for the production of valuable alkyl phenols and anilines has been developed based on the selective hydrodeoxygenation of a wide range of hydroxy-, amino-, and nitro-acetophenone derivatives as readily available substrates. Bimetallic iron ruthenium nanoparticles immobilized on an imidazolium-based supported ionic liquid phase (Fe25Ru75@SILP) act as highly active and selective catalysts for the deoxygenation of the side-chain without hydrogenation of the aromatic ring. The catalytic system allows operation under continuous flow conditions with high robustness and flexibility as demonstrated for the alternating conversion of 3′,5′-dimethoxy-4′-hydroxyacetophenone and 4′-hydroxynonanophenone as model substrates.
Selective Reduction of Nitroarenes to Arylamines by the Cooperative Action of Methylhydrazine and a Tris(N-heterocyclic thioamidate) Cobalt(III) Complex
Ioannou, Dimitris I.,Gioftsidou, Dimitra K.,Tsina, Vasiliki E.,Kallitsakis, Michael G.,Hatzidimitriou, Antonios G.,Terzidis, Michael A.,Angaridis, Panagiotis A.,Lykakis, Ioannis N.
, p. 2895 - 2906 (2021/02/27)
We report an efficient catalytic protocol that chemoselectively reduces nitroarenes to arylamines, by using methylhydrazine as a reducing agent in combination with the easily synthesized and robust catalyst tris(N-heterocyclic thioamidate) Co(III) complex [Co(κS,N-tfmp2S)3], tfmp2S = 4-(trifluoromethyl)-pyrimidine-2-thiolate. A series of arylamines and heterocyclic amines were formed in excellent yields and chemoselectivity. High conversion yields of nitroarenes into the corresponding amines were observed by using polar protic solvents, such as MeOH and iPrOH. Among several hydrogen donors that were examined, methylhydrazine demonstrated the best performance. Preliminary mechanistic investigations, supported by UV-vis and NMR spectroscopy, cyclic voltammetry, and high-resolution mass spectrometry, suggest a cooperative action of methylhydrazine and [Co(κS,N-tfmp2S)3] via a coordination activation pathway that leads to the formation of a reduced cobalt species, responsible for the catalytic transformation. In general, the corresponding N-arylhydroxylamines were identified as the sole intermediates. Nevertheless, the corresponding nitrosoarenes can also be formed as intermediates, which, however, are rapidly transformed into the desired arylamines in the presence of methylhydrazine through a noncatalytic path. On the basis of the observed high chemoselectivity and yields, and the fast and clean reaction processes, the present catalytic system [Co(κS,N-tfmp2S)3]/MeNHNH2 shows promise for the efficient synthesis of aromatic amines that could find various industrial applications.
Fabrication of palladium nanocatalyst supported on magnetic eggshell and its catalytic character in the catalytic reduction of nitroarenes in water
?al??kan, Melike,Akay, Sema,Baran, Talat,Kayan, Berkant
, (2021/07/21)
Aromatic nitro compounds, which have good solubility in water, are highly toxic and non-biodegradable are one of the most important industrial pollutants and have negative effects on human health, aquatic life and the environment. Therefore, the elimination of these harmful organic compounds has become an issue of great importance. For this, in this study we have developed a palladium nanocatalyst supported on Fe3O4-coated eggshell and characterized by FT-IR, XRD, XPS, FE-SEM, TG/DTG, BET, TEM and EDS techniques (Pd-Fe3O4-ES). Also, the quantitative analysis of Pd was determined using ICP-OES. The catalytic behavior of the designed Pd-Fe3O4-ES nanocatalyst was investigated against the catalytic reduction of several highly toxic nitro compounds using NaBH4 in water at room temperature. The progress of the reduction was followed using high performance liquid chromatography (HPLC). The catalytic studies revealed that the nitro compounds were converted into the desired amines by the Pd-Fe3O4-ES nanocatalyst using a very low dose of catalyst (15 mg) and short-duration reactions (81–360 s) in aqueous medium at ambient temperature. Furthermore, the Pd-Fe3O4-ES nanocatalyst showed good catalytic stability by retaining its activity after the fifth catalytic run.
