- A facile, one-pot procedure for forming diarylimines from nitroarenes and benzaldehydes
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An intermolecular reductive Schiff base formation from nitroarenes and benzaldehydes to yield diarylimines is carried out in the presence of iron powder and dilute acid. This process is tolerant of an array of functional groups and often proceeds quantitatively with no need for purification. Georg Thieme Verlag Stuttgart.
- Korich, Andrew L.,Hughes, Thomas S.
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- Catalyst- And solvent-free efficient access to: N -alkylated amines via reductive amination using HBpin
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A sustainable approach which works under catalyst- and solvent-free conditions for the synthesis of structurally diverse secondary amines has been uncovered. This one-pot protocol works efficiently at room temperature and is compatible with a wide range of sterically and electronically diverse aldehydes and primary amines. Notably, this simple process offers scalability, excellent functional group tolerance, chemoselectivity, and is also effective at the synthesis of biologically relevant molecules. This journal is
- Bauri, Somnath,Pandey, Vipin K.,Rit, Arnab
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supporting information
p. 3853 - 3857
(2020/07/27)
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- Thioglycerol-Stabilized Rhodium Nanoparticles in Biphasic Medium as Catalysts in Multistep Reactions
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Small rhodium nanoparticles (ca. 3.5 nm) were prepared by the decomposition of an organometallic precursor under hydrogen pressure in glycerol using 1-thioglycerol as stabilizer. Full characterization in the solid state [HR-TEM, EDX, XPS] showed a fcc structure for the Rh0/RhI nanoparticles capped with thiolate ligand. Reduction of different functionalities, including nitro groups and imines, was applied to tandem reductive amination of aldehydes with primary and secondary amines, and to the synthesis of N-substituted anilines from nitrobenzene. In addition, thiolate-capped RhNPs could be recovered and reused up to 5 runs without loss of activity nor selectivity.
- Guerrero-Ríos, Itzel,Portales-Martínez, Benjamín,Reina, Antonio,Serrano-Maldonado, Alejandro
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supporting information
(2020/07/04)
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- Bi-functional catalyst of porous N-doped carbon with bimetallic FeCu for solvent-free resultant imines and hydrogenation of nitroarenes
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The efficient and stable catalyst applied to the transformation of amines into the corresponding imines and hydrogenation of nitroarenes under mild reaction conditions is reported. The catalytic performance of porous N-doped carbon with FeCu (FeCu@NPC) catalyst are tested by aromatic alcohol-based N-alkylated of amines with solvent-free and hydrogenation of nitroarenes via N2H4·H2O. The results proved that the yield of these two reactions are all over 99.9% under optimum condition. Moreover, the synergistic effect of the catalyst for N-alkylated reaction was investigated through the kinetic study. The catalyst can be easily separated from reaction system by an external magnetism, and can be recycled and reutilized for at least 4 runs with conversions are all over 75%. The study of the catalyst indicated that it was suitable for the reactions in industry. Hence, the catalysis process by the inexpensive metals-based catalyst is green and sustainable.
- Wang, Kaizhi,Gao, Wenbing,Jiang, Pengbo,Lan, Kai,Yang, Ming,Huang, Xiaokang,Ma, Lei,Niu, Fang,Li, Rong
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- Effect of linker and metal on photoreduction and cascade reactions of nitroaromatics by M-UiO-66 metal organic frameworks
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The use of metal organic frameworks (MOFs) as photocatalysts is a promising and growing area of research. Given the diverse architectures, linkers, and metals, it is important to understand their effects on catalysis. Herein we compare six MOFs of the UiO-66 family towards photocatalytic reduction of nitro-aromatics to anilines. These MOFs differ in metal identity (Hf, Zr) and linker, and hence this systematic study provides insights to developing next generation MOFs. We found that Hf-based MOFs are superior to the more commonly studied Zr-analogues. Moreover, the linker identity also impact the photocatalysis, with pyridine-based linkers out-performing aniline based linkers and those that lack an embedded basic site. The MOFs studied have unique selectivities for the photoreduction and also allow for the one-pot synthesis of imines from aromatic aldehydes and nitro-aromatics.
- Elkin,Saouma
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supporting information
(2019/08/30)
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- Manganese catalyzed reductive amination of aldehydes using hydrogen as a reductant
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A one-pot two-step procedure was developed for the alkylation of amines via reductive amination of aldehydes using molecular dihydrogen as a reductant in the presence of a manganese pyridinyl-phosphine complex as a pre-catalyst. After the initial condensation step, the reduction of imines formed in situ is performed under mild conditions (50-100 °C) with 2 mol% of catalyst and 5 mol% of tBuOK under 50 bar of hydrogen. Excellent yields (>90%) were obtained for a large combination of aldehydes and amines (40 examples), including aliphatic aldehydes and amino-alcohols.
- Wei, Duo,Bruneau-Voisine, Antoine,Valyaev, Dmitry A.,Lugan, No?l,Sortais, Jean-Baptiste
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supporting information
p. 4302 - 4305
(2018/05/03)
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- Magnetic NiO nanoparticles confined within open ends MWCNTs: A novel and highly active catalyst for hydrogenation and synthesis of imines
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A new nanocatalyst has been synthesized by confining magnetic nickel nanoparticles within carbon nanotubes (CNTs) and characterized by XRD, TEM, Raman and VSM. The character of the nanocatalyst passivated with a gas mixture was that it can be stored safely in air below 150 °C and needs no activation prior to use. In the catalytic test, a nickel oxide nanocatalyst confined inside the Multi-walled carbon nanotubes nanochannels (NiO/MWCNTs-in) was found to be a highly efficient and reusable catalyst for the reduction of various aromatic nitro compounds to various aromatic amines, the conversion and selectivity of which were almost up to 100% and exceed 80%. The prominent merit of the catalyst is that the overall formation rate of product inside the nanotubes exceeds that outside. Moreover, it is inexpensive, and could be prepared and scaled up easily. Besides, it can be simply separated from the reaction mixtures by an external magnetic field As a result of the possible confinement effect of CNTs, the employment of the CNTs channels as nanoreactors for catalysis may provide opportunities for the development of new heterogeneous catalysts.
- Chen, Gangquan,Gao, Wenbin,Wang, Xuejun,Huo, Hongfei,Li, Wenzhu,Zhang, Le,Li, Rong,Li, Zuixiong
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p. 58805 - 58812
(2016/07/06)
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- General and selective reductive amination of carbonyl compounds using a core-shell structured Co3O4/NGr@C catalyst
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The application of heterogenized non-noble metal-based catalysts in selective catalytic hydrogenation processes is still challenging. In this respect, the preparation of a well-defined cobalt-based catalyst was investigated by immobilization of the corresponding cobalt(ii)-phenanthroline-chelate on Vulcan XC72R carbon powder. The formed core-shell structured cobalt/cobalt oxide nanocomposites are encapsulated by nitrogen-enriched graphene layers. This promising cheap heterogeneous catalyst allows for an efficient domino reductive amination of carbonyl compounds with nitroarenes. This journal is
- Stemmler, Tobias,Westerhaus, Felix A.,Surkus, Annette-Enrica,Pohl, Marga-Martina,Junge, Kathrin,Beller, Matthias
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p. 4535 - 4540
(2014/12/10)
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- Iron-catalyzed synthesis of secondary amines: On the way to green reductive aminations
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Amines represent important intermediates in chemical and biological processes. Herein, we describe the use of a nanostructured iron-based catalyst for the tandem reductive amination between nitroarenes and aldehydes using hydrogen as reductant. The nanostructured iron-catalyst is prepared by immobilization of an iron-phenanthroline complex onto a commercially available carbon support. In the reaction sequence a primary amine is formed in situ from the corresponding nitro compound. Reversible condensation with aldehydes forms the respective imines, which are finally reduced to the desired secondary amine. This synthesis of secondary amines is atom-economical and environmentally attractive using cheap and readily available organic compounds as starting materials.
- Stemmler, Tobias,Surkus, Annette-Enrika,Pohl, Marga-Martina,Junge, Kathrin,Beller, Matthias
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p. 3012 - 3016
(2015/09/28)
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- METHOD FOR THE CATALYTIC REDUCTION OF ACID CHLORIDES AND IMIDOYL CHLORIDES
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The present application relates to methods for the catalytic reduction of acid chlorides and/or imidoyl chlorides. The methods comprise reacting the acid chloride or imidoyl chloride with a silane reducing agent in the presence of a catalyst such as [Cp(Pri3P)Ru(NCMe)2]+[PF6]?.
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- Mild and efficient PtO2-catalyzed one-pot reductive mono-N-alkylation of nitroarenes
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(Chemical Equation Presented) A mild and efficient one-pot reductive monoalkylation of nitroarenes has been described using aldehydes as alkylating agents, molecular hydrogen as a reducing agent, and PtO2 as a catalyst in methanol. This methodology is found to be applicable for both aliphatic and aromatic aldehydes and for a wide variety of nitroarenes. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Commuications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Sreedhar, Bojja,Rawat, Vikas S.
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experimental part
p. 2490 - 2502
(2012/07/14)
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- Direct one-pot reductive imination of nitroarenes using aldehydes and carbon monoxide by titania supported gold nanoparticles at room temperature
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The direct one-pot reductive imination of nitroarenes with various aldehydes by a titania supported gold catalyst at room temperature using CO/H2O as a reducing agent is illustrated. This method is simple, economic, general and environmentally benign, thus resulting in practical advantages for the synthesis of imines and their derivatives.
- Huang, Jun,Yu, Lei,He, Lin,Liu, Yong-Mei,Cao, Yong,Fan, Kang-Nian
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supporting information; experimental part
p. 2672 - 2677
(2011/11/06)
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- Chemoselectivity in reactions of an α-diazo-β-diketone with some conjugative double-bond systems
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Reactions of 2-diazo-1,3-diphenylpropane-1,3-dione with α,β-unsaturated aldehydes and ketones, and keto-imines, in refluxing anhydrous toluene indicate that benzoyl(phenyl)ketene, which is generated by the thermal Wolff rearrangement of 2-diazo-1,3-diphen
- Xu,Zhang,Chen,Chen
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p. 2266 - 2268
(2007/10/03)
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