3544-25-0Relevant academic research and scientific papers
Cyanomethylation of the Benzene Rings and Pyridine Rings via Direct Oxidative Cross-Dehydrogenative Coupling with Acetonitrile
Lin, Sen,Wang, Bingqing,Yan, Zhaohua,Yao, Hua,Zhong, Xiaoyang
supporting information, p. 2030 - 2034 (2022/03/31)
A novel and efficient approach for the amine-directed dehydrogenative C(sp2)-C(sp3) coupling of arylamines with acetonitrile was reported by using FeCl2as the catalyst. Substituted anilines, aminopyridines, naphthylamines, and some nitrogen-containing heterocyclic arylamines react with inactive acetonitrile to form the corresponding arylacetonitriles in moderate to good yields. This protocol features nontoxic iron catalysis, efficient atom economy, nonprefunctionalized starting materials, good regioselectivity, and excellent compatibility of functional groups and aromatic rings, providing a novel, straightforward, and green approach toward arylacetonitriles.
A mild and selective Cu(II) salts-catalyzed reduction of nitro, azo, azoxy, N-aryl hydroxylamine, nitroso, acid halide, ester, and azide compounds using hydrogen surrogacy of sodium borohydride
Kalola, Anirudhdha G.,Prasad, Pratibha,Mokariya, Jaydeep A.,Patel, Manish P.
supporting information, p. 3565 - 3589 (2021/10/12)
The first mild, in situ, single-pot, high-yielding well-screened copper (II) salt-based catalyst system utilizing the hydrogen surrogacy of sodium borohydride for selective hydrogenation of a broad range of nitro substrates into the corresponding amine under habitancy of water or methanol like green solvents have been described. Moreover, this catalytic system can also activate various functional groups for hydride reduction within prompted time, with low catalyst-loading, without any requirement of high pressure or molecular hydrogen supply. Notably, this system explores a great potential to substitute expensive traditional hydrogenation methodologies and thus offers a greener and simple hydrogenative strategy in the field of organic synthesis.
Monolithic Silica Support for Immobilized Catalysis in Continuous Flow
Russell, M. Grace,Veryser, Cedrick,Hunter, James F.,Beingessner, Rachel L.,Jamison, Timothy F.
supporting information, p. 314 - 319 (2019/12/24)
Monolithic and packed-bed reactors featuring immobilized catalysts are well-precedented in continuous flow synthesis but can suffer from adverse pressure drops during use due to their small pore sizes and/or structural changes. Herein, we overcome this challenge with the synthesis of a structurally robust silica-based monolith featuring pore sizes on the millimeter scale. The 3-dimensional solid support structure is constructed from a polystyrene foam-based template and features a functional group handle that can be modified to display a reactive catalyst. Here we functionalize the support with palladium(0) for hydrogenation reactions and a modified proline catalyst for the alpha functionalization of aldehydes. Both reactors showed good activity and excellent catalytic longevity when utilized under continuous flow conditions. (Figure presented.).
Ultrasound-assisted rapid reduction of nitroaromatics to anilines using gallium metal
Bento, Ian,Bernaldez, Mabel,Noguchi, Ryden,Kawakami, Joel
supporting information, p. 1404 - 1407 (2020/03/31)
The reduction of nitroaromatic compounds to anilines is widely used throughout organic synthesis. Typical methods of performing this transformation utilize hydrogenation over a pyrophoric catalyst or a finely divided reducing metal, which often affords heterogeneous mixtures that are difficult to purify. Herein, we report for the first time the use of gallium metal as a reducing agent in organic synthesis. The reaction proceeds under aerobic conditions and affords homogeneous mixtures for a convenient workup. Using this method, twelve anilines were obtained in 33% to quantitative yields with short reaction times of 10-60 minutes.
Simple reversible fixation of a magnetic catalyst in a continuous flow system: Ultrafast reduction of nitroarenes and subsequent reductive amination using ammonia borane
Byun, Sangmoon,Cho, Ahra,Kang, Dong Yun,Kim, B. Moon,Kim, Ha Joon,Kim, Hong Won,Kim, Seong Min,Lei, Cao,Park, Jin Kyoon
, p. 944 - 949 (2020/03/11)
Continuous reductive amination of aldehydes with nitroarenes over a Pd-Pt-Fe3O4 catalyst was performed. We used NH3BH3 as not only a hydrogen source for nitro reduction, but also a reductant for imine reduction. Secondary aromatic amines were obtained in the continuous flow reaction in good to excellent yields.
Preparation method of arylamine compound
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Paragraph 0036-0043, (2020/12/10)
The invention belongs to the technical field of natural compounds, pharmaceutical and chemical intermediates and related chemistry, and provides a preparation method of arylamine compounds. The methoduses aromatic nitro compounds as raw materials, a nano porous platinum-iron catalyst as a catalyst and hydrogen as a hydrogen source to prepare arylamine through selective hydrogenation. The adoptedcatalyst is the nano porous platinum-iron catalyst, the pore size is 1nm-50nm, and the molar ratio of the aromatic nitro compound to the catalyst is 1:0.01-1:0.5; the pressure of the hydrogen is 0.1-20.0 MPa; and the molar concentration of the nitro compound in the solvent is 0.01-2 mmol/mL. The method has the beneficial effects that the reaction conditions are very mild, the product selectivity is high, the operation and post-treatment are simple, the catalyst activity is high, the property is stable, the price is low, the reproducibility is good, the catalytic effect is not obviously reducedafter repeated use for multiple times, and the possibility is provided for industrialization.
Hydrogenation of nitroarenes to anilines in a flow reactor using polystyrene supported rhodium in a catalyst-cartridge (Cart-Rh@PS)
Sharma, Saurabh,Yamini,Das, Pralay
supporting information, p. 1764 - 1769 (2019/01/28)
The present methodology described the chemo-selective hydrogenation of various nitroarenes in a flow reactor under polystyrene supported rhodium in a catalyst-cartridge (Cart-Rh@PS) as a heterogeneous nano-catalyst. The polystyrene supported Rh (Rh@PS) nanoparticles (NPs) were prepared by following our earlier reported protocol and packed inside the catalyst-cartridge (Cat-Cart) to obtain Cart-Rh@PS, which is compatible with ThalesNano's H-Cube Pro flow system. The advantages of the prepacked catalyst Cart-Rh@PS are as follows: no need for catalyst activation up to 12 runs, negligible metal leaching detected by ICP-AES analysis and significantly less back pressure generated under the flow conditions. The same catalyst, Cart-Rh@PS, was also effective up to a 1 gram scale for the reduction of nitroarenes and reusable for successive runs. The hydrogenation in the flow reactor is a greener approach for the reduction of nitroarenes to their corresponding anilines in high yields.
Hydrogenation of nitroarenes catalyzed by a dipalladium complex
Hung, Ming-Uei,Yang, Shu-Ting,Ramanathan, Mani,Liu, Shiuh-Tzung
, (2017/09/06)
A dipalladium complex [Pd2(L)Cl2](PF6)2 (2), via the substitution of (PhCN)2PdCl2 with 5-phenyl-2,8-bis(6′-bipyridinyl)-1,9,10-anthyridine (L) followed by the anion exchange, was found to be a good pre-catalyst for the reduction of nitroarenes to yield the corresponding anilines under atmospheric pressure of hydrogen in methanol. This method provides a straightforward access to a diverse array of functionalized anilines, exhibiting a possible application in synthetic chemistry. The catalytic activity of this complex is enhanced by the di-metallic system via the synergistic effect.
Preparation method of apatinib
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Paragraph 0083; 0091; 0092; 0093; 0094, (2018/09/11)
The invention discloses a preparation method of apatinib and belongs to the field of medicine and fine chemical industry. The preparation method is a novel preparation scheme; a target compound that is satisfactory can be acquired with any intermediate. The preparation method has the advantages the advantages of short procedure, simple reacting steps, good safety and reliability, high yield, low cost, high purity, low pollution, good operational simplicity and the like.
Preparation of Well-Ordered Mesoporous-Silica-Supported Ruthenium Nanoparticles for Highly Selective Reduction of Functionalized Nitroarenes through Transfer Hydrogenation
Wei, Ning,Zou, Xiujing,Huang, Haigen,Wang, Xueguang,Ding, Weizhong,Lu, Xionggang
supporting information, p. 209 - 214 (2018/01/26)
MCM-41-type mesoporous silica (OMS-IL) was prepared by using an ionic liquid (1-hexadecyl-3-methylimidazolium bromide) as a template. The XRD and TEM results demonstrated that OMS-IL was more stable than the MCM-41 material. Ru nanoparticles were supported on OMS-IL (Ru/OMS-IL) by impregnating OMS-IL with a RuCl3 aqueous solution, and the resulting material was used for the selective reduction of nitroarenes. The effects of the components of the catalysts and the reaction conditions on the catalytic behavior of the prepared catalysts were investigated in detail. Ru/OMS-IL exhibited high catalytic activity and chemoselectivity for the reduction of various substituted nitroarenes to the corresponding aromatic amines in ethanol with hydrazine hydrate as a hydrogen donor under mild conditions. The Ru/OMS-IL catalysts were highly stable and could easily be recovered by simple filtration over at least six recycling reactions without any observable loss in catalytic performance.
