24005-23-0Relevant articles and documents
Phosphonium-stibonium and bis-stibonium cations as pnictogen-bonding catalysts for the transfer hydrogenation of quinolines
Yang, Mengxi,Hirai, Masato,Gabba?, Fran?ois P.
, p. 6685 - 6689 (2019)
Bifunctional Lewis acidic group 15 compounds have emerged as appealing platforms for anion sensing and organocatalysis. As part of our interest in the chemistry of these compounds, we have now compared the catalytic properties of [o-(MePPh2)Cs
Deciphering a Reaction Network for the Switchable Production of Tetrahydroquinoline or Quinoline with MOF-Supported Pd Tandem Catalysts
Bao, Zongbi,Chen, Jingwen,Huang, Wenyu,Kobayashi, Takeshi,Nie, Renfeng,Qi, Long,Qi, Zhiyuan,Ren, Qilong,Sun, Qi,Yang, Qiwei,Zhang, Biying,Zhang, Zhiguo
, p. 5707 - 5714 (2020)
A mechanistic study of heterogeneous tandem catalytic systems is crucial for understanding and improving catalyst activity and selectivity but remains challenging. Here, we demonstrate that a thorough mechanistic study of a multistep reaction can guide us to the controllable selective synthesis of phenyltetrahydroquinoline or phenylquinoline with easily accessible precursors. The one-pot production can be achieved, catalyzed by a well-defined, bifunctional metal-organic framework-supported Pd nanoparticles, with only water as the side product. Our mechanistic study identifies six transient intermediates and ten transformation steps from the operando magic angle spinning nuclear magnetic resonance study under 27.6 bar H2. In particular, reactive intermediate 2-phenyl-3,4-dihydroquinoline cannot be observed with conventional chromatographic techniques but is found to reach the maximal concentration of 0.11 mol L-1 under the operando condition. The most probable reaction network is further deduced based on the kinetic information of reaction species, obtained from both operando and ex situ reaction studies. This deep understanding of the complex reaction network enables the kinetic control of the conversions of key intermediate, 2-phenyl-3,4-dihydroquinoline, with the addition of a homogeneous co-catalyst, allowing the selective production of tetrahydroquinoline or quinoline on demand. The demonstrated methods in this work open up new avenues toward efficient modulation of reactions with a complex network to achieve desired selectivities.
Liberating N-CNTs Confined Highly Dispersed Co?Nx Sites for Selective Hydrogenation of Quinolines
Gong, Wanbing,Yuan, Qinglin,Chen, Chun,Lv, Yang,Lin, Yue,Liang, Changhao,Wang, Guozhong,Zhang, Haimin,Zhao, Huijun
, (2019)
Selective hydrogenation of quinoline and its derivatives is an important means to produce corresponding 1,2,3,4-tetrahydroquinolines for a wide spectrum of applications. A facile and efficient “laser irradiation in liquid” technique to liberate the inaccessible highly dispersed Co?Nx active sites confined inside N-doped carbon nanotubes is demonstrated. The liberated Co?Nx sites possess generic catalytic activities toward selective hydrogenation of quinoline and its hydroxyl, methyl, and halogen substituted derivatives into corresponding 1,2,3,4-tetrahydroquinolines with almost 100% conversion efficiency and selectivity. This laser irradiation treatment approach should be widely applicable to unlock the catalytic powers of inaccessible catalytic active sites confined by other materials.
Tuning porosity and activity of microporous polymer network organocatalysts by co-polymerisation
Schmidt, Johannes,Kundu, Dipti Sankar,Blechert, Siegfried,Thomas, Arne
, p. 3347 - 3349 (2014)
Microporous polymer networks based on binaphthyl phosphoric acids are suitable heterogeneous asymmetric organocatalysts. Herein we show that the porous characteristics of such networks can be fine-tuned by co-polymerisation. This enables us to investigate the influence of the surface area and porosity in microporous networks on their catalytic performance. In this case, the activity of the polymers in an asymmetric hydrogenation reaction is increased by the use of polymers with higher surface areas. The Royal Society of Chemistry 2014.
PREPARATION METHOD OF 2-SUBSTITUTED 1,2,3,4-TETRAHYDROQUINOLINE COMPOUND
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Paragraph 0111-0121, (2021/08/05)
2 -substituted quinoline compounds are disclosed. The present invention relates to a 2 -substituted 2 -tetrahydroquinoline compound by hydroconversion of 1, 2, 3, 4 -substituted quinoline compounds using a catalyst composition comprising an isothiuronium salt and a Handoesr. In accordance with the present invention, 2 -substituted 1, 2, 3, 4 -tetrahydroquinoline compounds can be produced in high yield with improved reaction efficiency and reaction rate.
Synthesis of Fused Heterocyclic Systems Derived from 2-Aryl-1,2,3,4-tetrahydroquinolines
Baimuratov, M. R.,Golovko, Yu. A.,Gruzd, Yu. A.,Klimochkin, Yu. N.,Kulemina, S. V.,Zemtsova, M. N.
, p. 793 - 800 (2021/06/12)
Abstract: A convenient method of synthesis of fused heterocyclic systems, involving cyclization of the reaction products of 2-aryl-1,2,3,4-tetrahydroquinolines with triphosgene, chloroacetyl chloride, and oxalyl chloride in the presence of anhydrous AlCl
Tuning the Catalytic Performance of Cobalt Nanoparticles by Tungsten Doping for Efficient and Selective Hydrogenation of Quinolines under Mild Conditions
Concepción, Patricia,Corma, Avelino,Liu, Lichen,Puche, Marta,Sorribes, Iván
, p. 8197 - 8210 (2021/07/13)
Non-noble bimetallic CoW nanoparticles (NPs) partially embedded in a carbon matrix (CoW@C) have been prepared by a facile hydrothermal carbon-coating methodology followed by pyrolysis under an inert atmosphere. The bimetallic NPs, constituted by a multishell core-shell structure with a metallic Co core, a W-enriched shell involving Co7W6 alloyed structures, and small WO3 patches partially covering the surface of these NPs, have been established as excellent catalysts for the selective hydrogenation of quinolines to their corresponding 1,2,3,4-tetrahydroquinolines under mild conditions of pressure and temperature. It has been found that this bimetallic catalyst displays superior catalytic performance toward the formation of the target products than the monometallic Co@C, which can be attributed to the presence of the CoW alloyed structures.
