- The preparation of a Co@C3N4catalyst and applications in the synthesis of quinolines from 2-aminobenzyl alcohols with ketones
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An unsymmetrical diphenylphosphino-pyridinyl-triazole ligand was synthesized and characterized through IR, NMR and MS and the corresponding earth-abundant metal complex (cobalt) was prepared. Considering energy consumption and environmental friendliness, it is necessary to turn this diphenylphosphino-pyridinyl-triazole cobalt complex into a recyclable catalyst, which could easily be reused. Therefore, a heterogeneous catalyst was synthesized through Co-doping of C3N4, and the Co-nanoparticles on C3N4revealed high catalytic activity for the synthesis of quinolines with good recovery performance.
- Cao, Fei,Mao, Anruo,Yang, Bobin,Ge, Chenyang,Wang, Dawei
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supporting information
p. 6768 - 6772
(2021/04/22)
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- Kinetic Resolution of 2,2-Disubstituted Dihydroquinolines through Chiral Phosphoric Acid-Catalyzed C6-Selective Asymmetric Halogenations
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A novel kinetic resolution of 2,2-disubstituted dihydroquinolines was achieved by regioselective asymmetric halogenations enabled by chiral phosphoric acid catalysis. A series of dihydroquinolines bearing 2,2-disubstitutions were well-tolerated in these reactions, generating both the recovered dihydroquinolines and C-6-brominated products with high enantioselectivities, with s-factors up to 149. In addition, this kinetic resolution protocol is also applicable for 2,2-disubstituted tetrahydroquinoline and asymmetric iodonation reaction.
- Chen, Yunrong,He, Yu-Peng,Liu, Wei,Tao, Houchao,Yang, Xiaoyu,Zhao, Fei,Zhu, Chaofan
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supporting information
p. 4104 - 4108
(2021/06/27)
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- Modular Access to Spiro-dihydroquinolines via Scandium-Catalyzed Dearomative Annulation of Quinolines with Alkynes
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The catalytic enantioselective construction of three-dimensional molecular architectures from planar aromatics such as quinolines is of great interest and importance from the viewpoint of both organic synthesis and drug discovery, but there still exist many challenges. Here, we report the scandium-catalyzed asymmetric dearomative spiro-annulation of quinolines with alkynes. This protocol offers an efficient and selective route for the synthesis of spiro-dihydroquinoline derivatives containing a quaternary carbon stereocenter with an unprotected N-H group from readily accessible quinolines and diverse alkynes, featuring high yields, high enantioselectivity, 100% atom-efficiency, and broad substrate scope. Experimental and density functional theory studies revealed that the reaction proceeded through the C-H activation of the 2-aryl substituent in a quinoline substrate by a scandium alkyl (or amido) species followed by alkyne insertion into the Sc-aryl bond and the subsequent dearomative 1,2-addition of the resulting scandium alkenyl species to the C=N unit in the quinoline moiety. This work opens a new avenue for the dearomatization of quinolines, leading to efficient and selective construction of spiro molecular architectures that were previously difficult to access by other means.
- Lou, Shao-Jie,Luo, Gen,Yamaguchi, Shigeru,An, Kun,Nishiura, Masayoshi,Hou, Zhaomin
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supporting information
p. 20462 - 20471
(2021/12/03)
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- Enantioselective Synthesis of Tetrahydroquinolines via One-Pot Cascade Biomimetic Reduction?
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A novel and efficient protocol for the synthesis of chiral tetrahydroquinoline derivatives with excellent enantioselectivities and high yields has been developed through one-pot cascade biomimetic reduction. The detailed reaction pathway includes the acid-catalyzed and ruthenium-catalyzed formation of aromatic quinoline intermediates and biomimetic asymmetric reduction.
- Zhao, Zi-Biao,Li, Xiang,Chen, Mu-Wang,Wu, Bo,Zhou, Yong-Gui
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supporting information
p. 1691 - 1695
(2020/11/03)
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- Organometal-Free Arylation and Arylation/Trifluoroacetylation of Quinolines by Their Reaction with CF3-ynones and Base-Induced Rearrangement
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The reaction of quinolines with CF3-ynones resulted in the formation of 1,3-oxazinoquinolines. Subsequent treatment of the reaction mixture with a base initiated deep structural transformation of primary products. Both steps proceed in very high yield. As a result, unusual rearrangement of 1,3-oxazinoquinolines to form either 2-arylquinolines or 2-aryl-3-trifluoroacetylquinolines was discovered. The decisive role of the base in the reaction direction was shown. Using these reactions, highly efficient pathways to 2-arylquinolines and 2-aryl-3-trifluoroacetylquinolines were elaborated to provide the corresponding compounds in high yields using a simple one-pot procedure. The possible mechanism of rearrangement is discussed.
- Muzalevskiy, Vasiliy M.,Belyaeva, Kseniya V.,Trofimov, Boris A.,Nenajdenko, Valentine G.
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p. 9993 - 10006
(2020/09/09)
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- Preparation of 2-Arylquinolines from 2-Arylethyl Bromides and Aromatic Nitriles with Magnesium and N -Iodosuccinimide
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Treatment of 2-arylethylmagnesium bromides, prepared from 2-arylethyl bromides and magnesium, with aromatic nitriles, followed by reaction with water and then with N -iodosuccinimide under irradiation with a tungsten lamp, gave the corresponding 2-arylquinolines in good to moderate yields under transition-metal-free conditions. 2-Alkylquinolines could be also obtained in moderate yields by the same procedure with 2-arylethyl bromides, magnesium, aliphatic nitriles bearing a secondary alkyl group, and N -iodosuccinimide.
- Naruto, Hiroki,Togo, Hideo
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p. 1122 - 1130
(2020/04/01)
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- Pd-Catalyzed Tandem Reaction of 2-Aminostyryl Nitriles with Arylboronic Acids: Synthesis of 2-Arylquinolines
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A novel palladium-catalyzed protocol for the synthesis of 2-arylquinolines via tandem reaction of 2-aminostyryl nitriles with arylboronic acids has been developed with good functional group tolerance. The presented approach offers a new synthetic pathway toward the core structures of 2-arylquinolines compared to classical condensation reaction of (E)-2-aminostyryl aryl ketones. Moreover, the present synthetic route could be readily scaled up to gram quantity without difficulty. Preliminary mechanistic experiments showed that this transformation involves a nucleophilic addition of aryl palladium species to the nitrile to generate an aryl ketone intermediate followed by an intramolecular cyclization and dehydration to quinoline ring.
- Xu, Tong,Shao, Yinlin,Dai, Ling,Yu, Shulin,Cheng, Tianxing,Chen, Jiuxi
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p. 13604 - 13614
(2019/10/16)
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- Synergy of anodic oxidation and cathodic reduction leads to electrochemical deoxygenative C2 arylation of quinoline: N-oxides
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The first example of electrochemical deoxygenative C2 arylation of quinoline N-oxides using sulfonyl hydrazines was demonstrated in this work. By employing both anodic oxidation and cathodic reduction, a variety of 2-arylquinolines were synthesized under metal catalyst-, exogenous-oxidant-, and exogenous-reductant-free conditions.
- Yuan, Yong,Jiang, Minbao,Wang, Tao,Xiong, Yunkui,Li, Jun,Guo, Huijiao,Lei, Aiwen
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p. 11091 - 11094
(2019/09/20)
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- Copper-Catalyzed Aerobic Oxidative Cyclization of Anilines, Aryl Methyl Ketones and DMSO: Efficient Assembly of 2-Arylquinolines
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A Cu-catalyzed C?H cyclization of simple anilines with ketones and DMSO as a one-carbon source has been developed. Using an aerobic oxidative protocol, a number of ketones and anilines could be easily converted to 2-arylquinolines, rather than 4-arylquinolines, thus providing a highly atom-economical and simple approach to biologically significant 2-arylquinolines. Based on the preliminary experiments, a plausible mechanism is proposed. (Figure presented.).
- Liu, Yufeng,Hu, Yuqun,Cao, Zhongzhong,Zhan, Xi,Luo, Weiping,Liu, Qiang,Guo, Cancheng
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supporting information
p. 2691 - 2695
(2018/06/04)
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- Sequential Photoredox Catalysis for Cascade Aerobic Decarboxylative Povarov and Oxidative Dehydrogenation Reactions of N-Aryl α-Amino Acids
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A visible-light-driven sequential photoredox catalysis to allow N-aryl α-amino acids to experience efficient cascade aerobic decarboxylative Povarov and oxidative dehydrogenation (ODH) reactions is described. With a dicyanopyrazine-derived chromophore (DP
- Shao, Tianju,Yin, Yanli,Lee, Richmond,Zhao, Xiaowei,Chai, Guobi,Jiang, Zhiyong
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supporting information
p. 1754 - 1760
(2018/03/21)
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- Functional Mechanically Interlocked Molecules: Asymmetric Organocatalysis with a Catenated Bifunctional Br?nsted Acid
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Interlocked molecules, such as catenanes, rotaxanes, and molecular knots, have become interesting candidates for the development of sophisticated chemical catalysts. Herein, we report the first application of a catenane-based catalyst in asymmetric organo
- Mitra, Raja,Zhu, Hui,Grimme, Stefan,Niemeyer, Jochen
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supporting information
p. 11456 - 11459
(2017/09/12)
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- Palladium-Catalyzed Allylic C-H Oxidative Annulation for Assembly of Functionalized 2-Substituted Quinoline Derivatives
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An efficient and practical palladium-catalyzed aerobic oxidative approach to afford functionalized 2-substituted quinolines in moderate to good yields from readily available allylbenzenes with aniline is developed. The present annulation process has high functional-group tolerance and high atom economy, making it a valuable and practical method in synthetic and medicinal chemistry. Moreover, this transformation is supposed to proceed through oxidation of allylic C-H functionalization to form C-C and C-N bonds in one pot.
- Li, Chunsheng,Li, Jianxiao,An, Yanni,Peng, Jianwen,Wu, Wanqing,Jiang, Huanfeng
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p. 12189 - 12196
(2016/12/23)
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- New red phosphorescent iridium(III) complex with 4-tert-Butylphenyl-boronic acid of organic borane
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A new phosphorescent (CQ-BP)2Ir(acac), (CMQ-BP)2Ir(acac), (BQ-BP)2Ir(acac) was synthesized for organic light-emitting diodes (OLEDs). OLEDs using phosphorescent iridium(III) complexes attract enormous attention because they allow highly efficient electro phosphorescence. The donor-acceptor type ligands for the Iridium(III) complexes were synthesized by Suzuki coupling reaction. The ligands through changes in oxidative addition materials (electron-acceptor) and organic borane (electron-donor) to get the red color were to study the appropriate Iridium(III) complexes. Oxidative addition materials were used such as 2-chloro-4-methylquinoline, 1-chloroisoquinoline and 2-bromoquinoline. 4-tert-Butylphenyl-boronic acid was used as organic borane. The dopant was synthesized by Nonoyama reaction. Red dopants were observed with an emission peak at approximately 600?nm. Iridium(III) complexes were measured by nuclear magnetic resonance (NMR), UV-visible spectroscopy and photoluminescence (PL). The phosphorescence emission maxima were dependent on the electron density of donor and acceptor moiety of the ligands.
- Lee, Sang-Wook,Shin, Dong-Myung
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- ONO pincer type Pd(II) complexes: Synthesis, crystal structure and catalytic activity towards C-2 arylation of quinoline scaffolds
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Four new palladium(II) complexes featuring ONO pincer type hydrazone ligands were synthesized and characterized by spectroscopic and single-crystal XRD analysis. These complexes showed excellent catalytic activity towards the Suzuki-Miyaura cross coupling reaction of 2-chloroquinoline derivatives with various aryl boronic acids. The main advantages over previous methodologies include low catalyst loading, less problematic reaction media (H2O-DMF (80:20%)) and a lower reaction temperature of 60 °C for optimal performance.
- Arumugam, Vignesh,Kaminsky, Werner,Nallasamy, Dharmaraj
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p. 77948 - 77957
(2015/09/28)
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- Highly enantioselective spinol-derived phosphoric acid catalyzed transfer hydrogenation of diverse C=N-containing heterocycles
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A highly efficient and enantioselective hydrogenation of diversely substituted C=N-containing heterocyclic compounds such as 3-aryl-1,4-benzoxazines and 2-arylquinolines was experimentally explored by using 1,1′-spirobiindane-7,7′-diol-derived chiral phosphoric acids as the catalyst. This method provides straightforward access to the corresponding tetrahydroquinolines and dihydro-2H-1,4-benzothiazines in high yields (85-99%) with excellent enantioselectivities (91-99%). The attractive features of this procedure, which include mild reaction conditions, operational simplicity, relatively low catalyst loading (1 mol-%), and high levels of enantioselectivities, make it a useful approach for the practical synthesis of optically active nitrogen-containing aromatic heterocycles.
- Zhang, Yiliang,Zhao, Rong,Bao, Robert Li-Yuan,Shi, Lei
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supporting information
p. 3344 - 3351
(2015/05/20)
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- An efficient synthesis of quinolines via copper-catalyzed C-N cleavage
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An efficient method to synthesize substituted quinolines from ketones and 2-amino benzylamines is described. Copper-catalyzed C-N cleavage of amines followed by condensation with ketones deliver quinolines in moderate to high yields. The broad scope of su
- Xi, Long-Yi,Zhang, Ruo-Yi,Zhang, Lei,Chen, Shan-Yong,Yu, Xiao-Qi
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p. 3924 - 3930
(2015/03/30)
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- Enantioselective cooperative triple catalysis: Unique roles of Au(i)/amine/chiral Bronsted acid catalysts in the addition/ cycloisomerization/transfer hydrogenation cascade
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An enantioselective cooperative process involving the concerted/ simultaneous action of three different catalysts i.e. Au(i)/amine/chiral Bronsted acid catalysts has been realized for the synthesis of 2-substituted tetrahydroquinolines from 2-aminobenzaldehydes and terminal alkynes.
- Patil, Nitin T.,Raut, Vivek S.,Tella, Ramesh Babu
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supporting information
p. 570 - 572
(2013/02/22)
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