- Bis(imino)pyridines fused with 6- and 7-membered carbocylic rings as: N, N, N -scaffolds for cobalt ethylene polymerization catalysts
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The unsymmetrical diketone, 1,2,3,7,8,9,10-heptahydrocyclohepta[b]quinoline-4,6-dione, based on a central pyridine unit fused by both 6- and 7-membered rings, has been synthesized via a sequence of reactions including ruthenium-catalyzed coupling cyclization. Templating this diketone with a mixture of cobalt(ii) chloride hexahydrate and the corresponding aniline in acetic acid at reflux afforded five examples of carbocyclic-fused bis(arylimino)pyridine-cobalt(ii) chlorides (aryl = 2,6-Me2Ph Co1, 2,6-Et2Ph Co2, 2,6-i-Pr2Ph Co3, 2,4,6-Me3Ph Co4, 4-Me-2,6-Et2Ph Co5) in good yield. All cobalt complexes have been fully characterized including by 1H NMR spectroscopy which reveals broad but assignable paramagnetically shifted peaks. The molecular structures of Co1, Co3 and Co4 highlight the inequivalency of the two fused rings with the cobalt center adopting a distorted trigonal bipyramidal geometry. Treatment of Co1-Co5 with MAO gave highly active catalysts (up to 5.03 × 106 g PE mol-1 (Co) h-1 at 40 °C, with Co4 > Co5 > Co1 > Co2 > Co3) for ethylene polymerization generating strictly linear vinyl-terminated polymers with low molecular weights (Mw range: 1.53-22.77 kg mol-1). By comparison, polymerizations conducted using Co1-Co5/MMAO were less active and displayed a lower selectivity for unsaturated polymers. Common to both MAO and MMAO, the most sterically hindered precatalyst Co3 gave the highest molecular weight polymer of the series (up to 22.77 kg mol-1) but exhibited the lowest activity.
- Wang, Zheng,Ma, Yanping,Guo, Jingjing,Liu, Qingbin,Solan, Gregory A.,Liang, Tongling,Sun, Wen-Hua
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- Direct synthesis of ring-fused quinolines and pyridines catalyzed byNNHY-ligated manganese complexes (Y = NR2or SR)
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Four cationic manganese(i) complexes, [(fac-NNHN)Mn(CO)3]Br (Mn-1-Mn-3) and [(fac-NNHS)Mn(CO)3]Br (Mn-4) (whereNNHis a 5,6,7,8-tetrahydro-8-quinolinamine moiety), have been synthesized and evaluated as catalysts for the direct synthesis of quinolines and pyridines by the reaction of a γ-amino alcohol with a ketone or secondary alcohol;NNHS-ligatedMn-4proved the most effective of the four catalysts. The reactions proceeded well in the presence of catalyst loadings in the range 0.5-5.0 mol% and tolerated diverse functional groups such as alkyl, cycloalkyl, alkoxy, chloride and hetero-aryl. A mechanism involving acceptorless dehydrogenation coupling (ADC) has been proposed on the basis of DFT calculations and experimental evidence. Significantly, this manganese-based catalytic protocol provides a promising green and environmentally friendly route to a wide range of synthetically important substituted monocyclic, bicyclic as well as tricyclicN-heterocycles (including 50 quinoline and 26 pyridine examples) with isolated yields of up to 93%.
- Han, Mingyang,Lin, Qing,Liu, Qingbin,Liu, Song,Ma, Ning,Solan, Gregory A.,Sun, Wen-Hua,Wang, Zheng,Yan, Xiuli
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p. 8026 - 8036
(2021/12/27)
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- Pincerlike manganese complex and preparation method thereof, related ligand and preparation method thereof, catalyst composition and application
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The invention discloses a pincerlike manganese complex, a preparation method thereof, a ligand for preparation, a preparation method of the ligand, a catalyst composition taking the complex as an active component and application of the catalyst composition. According to the pincerlike manganese complex, a cycloalkyl ring is introduced into a ligand framework, and by regulating and controlling the cyclic tension, flexibility and steric hindrance of the cycloalkyl ring, the reactivity and stability of the manganese metal center can be effectively adjusted, and the catalytic activity and substrate applicability of a manganese metal system are remarkably improved. The catalyst composition taking the pincerlike manganese complex as an active component has the advantages of high catalyst activity, wide substrate application range, mild reaction conditions and the like in the process of preparing quinoline or pyridine derivatives by catalyzing dehydrogenation coupling reaction of o-amino aromatic alcohol or gamma-amino alcohol, ketone or secondary alcohol; and the synthesis advantages of low cost and stable performance are embodied, the operation is simple, and the yield is high.
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Paragraph 0137-0143
(2021/07/31)
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- Efficient access to quinolines and quinazolines by ruthenium complexes catalyzed acceptorless dehydrogenative coupling of 2-aminoarylmethanols with ketones and nitriles
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Treatment of N,N,O-tridentate pyrazolyl-pyridinyl-alcohol ligands, 2-(CR1R2OH)-6-[3,5-(R3)2C3HN2]C5H3N (R1 = R2 = Me, R3 = H (L1H); R1 = Me, R2 = Ph, R3 = H (L2H); R1 = R2 = Ph, R3 = H (L3H); R1 = R2 = R3 = Me (L4H)) with RuCl3?xH2O in refluxing EtOH afforded the corresponding Ru(III) complexes L2RuCl (1a-1d), which were well characterized by IR, HR-MS and X-ray single crystal structural determination. These Ru complexes showed similarly high catalytic performance for both dehydrogenative couplings of 2-aminoarylmethanols with ketones and nitriles, giving the quinolines and quinazolines in good to excellent yields. This protocol provides an atom-economical and sustainable route to access various structurally important quinoline and quinazoline derivatives by using phosphine-free ligand based Ru catalysts.
- Huo, Shuaicong,Kong, Siqi,Zeng, Guang,Feng, Qi,Hao, Zhiqiang,Han, Zhangang,Lin, Jin,Lu, Guo-Liang
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- Half-Sandwich Ruthenium Complexes for One-Pot Synthesis of Quinolines and Tetrahydroquinolines: Diverse Catalytic Activity in the Coupled Cyclization and Hydrogenation Process
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Four types of half-sandwich ruthenium complexes with an N,O-coordinate mode based on hydroxyindanone-imine ligands have been prepared in good yields. These stable ruthenium complexes exhibited high activity in the catalytic synthesis of quinolines from the reactions of amino alcohols with different types of ketones or secondary alcohols under very mild conditions. Moreover, the methodology for the direct one-pot synthesis of tetrahydroquinoline derivatives from amino alcohols and ketones has been also developed on the basis of the continuous catalytic activity of this ruthenium catalyst in the selective hydrogenation of the obtained quinoline derivatives with a low catalyst loading. The corresponding products, quinolines and tetrahydroquinoline derivatives, were afforded in good to excellent yields. The efficient and diverse catalytic activity of these ruthenium complexes suggested their potential large-scale application. All of the ruthenium complexes were characterized by various spectroscopies to confirm their structures.
- Yun, Xue-Jing,Zhu, Jing-Wei,Jin, Yan,Deng, Wei,Yao, Zi-Jian
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supporting information
p. 7841 - 7851
(2020/06/04)
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- Synthesis of Pyridines, Quinolines, and Pyrimidines via Acceptorless Dehydrogenative Coupling Catalyzed by a Simple Bidentate P^ N Ligand Supported Ru Complex
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A ruthenium hydrido chloride complex (1) supported by a simple, heteroleptic bidentate P^N ligand (L1) containing a diarylphosphine and a benzannulated phenanthridine donor arm is reported. In the presence of base, complex 1 catalyzes multicomponent reactions using alcohol precursors to produce structurally diverse molecules including pyridines, quinolines, and pyrimidines via acceptorless dehydrogenative coupling pathways. Notably, L1 does not bear readily (de)protonated Br?nsted acidic or basic groups common to transition metal catalysts capable of these sorts of transformations, suggesting metal-ligand cooperativity does not play a significant role in the catalytic reactivity of 1. A rare example of an η2-aldehyde adduct of ruthenium was isolated and structurally characterized, and its role in acceptorless dehydrogenative coupling reactions is discussed.
- Mondal, Rajarshi,Herbert, David E.
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supporting information
p. 1310 - 1317
(2020/04/15)
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- Homogeneous Nickel-Catalyzed Sustainable Synthesis of Quinoline and Quinoxaline under Aerobic Conditions
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Dehydrogenative coupling-based reactions have emerged as an efficient route toward the synthesis of a plethora of heterocyclic rings. Herein, we report an efficacious, nickel-catalyzed synthesis of two important heterocycles such as quinoline and quinoxaline. The catalyst is molecularly defined, is phosphine-free, and can operate at a mild reaction temperature of 80 °C. Both the heterocycles can be easily assembled via double dehydrogenative coupling, starting from 2-aminobenzyl alcohol/1-phenylethanol and diamine/diol, respectively, in a shorter span of reaction time. This environmentally benign synthetic protocol employing an inexpensive catalyst can rival many other transition-metal systems that have been developed for the fabrication of two putative heterocycles. Mechanistically, the dehydrogenation of secondary alcohol follows clean pseudo-first-order kinetics and exhibits a sizable kinetic isotope effect. Intriguingly, this catalyst provides an example of storing the trapped hydrogen in the ligand backbone, avoiding metal-hydride formation. Easy regeneration of the oxidized form of the catalyst under aerobic/O2 oxidation makes this protocol eco-friendly and easy to handle.
- Bains, Amreen K.,Singh, Vikramjeet,Adhikari, Debashis
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p. 14971 - 14979
(2020/11/30)
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- Superbase-Mediated Indirect Friedl?nder Reaction: A Transition Metal-Free Oxidative Annulation toward Functionalized Quinolines
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A superbase mediated indirect Friedl?nder reaction towards functionalized quinolines has been realized. The reaction was performed with o-aminobenzyl alcohol and ketones having an active methylene moiety in the presence of KOH and in DMSO. The reaction proceeds predominantly via initial formation of an imine intermediate and subsequent oxidation of the benzyl alcohol functionality and condensation to afford substituted quinolines. We could also demonstrate that a minor fraction of the reaction proceeds via a chalcone intermediate. The transition metal-free oxidative annulation was found to be general affording 2-substituted, 2,3-disubstituted/fused or multi-substituted quinolines. The reaction was extended towards the functionalization of natural products and the applicability of the reaction for gram-scale synthesis of quinolines was also demonstrated.
- Rahul,Nitha,Omanakuttan, Vishnu K.,Babu, Sheba Ann,Sasikumar,Praveen, Vakayil K.,Hopf, Henning,John, Jubi
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p. 3081 - 3089
(2020/05/08)
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- Pyridylimine group complex containing asymmetric fused rings and preparation method and application of pyridylimine group complex
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The invention provides a pyridylimine group complex containing asymmetric fused rings and a preparation method and application of an intermediate of the pyridylimine group complex. The complex has high catalytic activity, can realize the regulation of the molecular weight of a polymer by changing a ligand structure and polymerization conditions, and has the advantages such as low cost and stable performance. The preparation method of the intermediate 2,3,7,8,9,10 hexahydro-1H-cycloheptaquinoline-4,6-dione compound and the complex has the advantages such as mild conditions, short cycle and simple operating conditions. The complex can be applied to a catalyst for ethylene polymerization, especially when an iron complex provided has high thermal stability, the catalytic activity can be as high as 15.86x10 g.mol(Fe)h under the action of a catalyst promoter MMAO, highly linear polyethylene is obtained, the catalytic activity can still be maintained at 5.44x10 g.mol(Fe)h even at a high temperature of 90 DEG C, the temperature is in line with the operating temperature of industrial production, and the pyridylimine group complex has good industrial application prospects.
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Paragraph 0114-0121
(2019/11/13)
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- Sustainable synthesis of N-heterocycles in water using alcohols following the double dehydrogenation strategy
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The present study describes the first example of synthesis of pharmaceutically relevant N-heterocycles like substituted quinolines, acridines and 1,8-naphthyridines in water under air using alcohols in presence of a new water soluble Ir-complex. The viability and efficiency of this approach was demonstrated by the efficient synthesis of biologically active natural product (±)-galipinine and gram scale synthesis of various N-heteroaromatics. Several kinetic experiments and DFT calculations were carried out to support the plausible reaction mechanism which disclosed that this system followed a concerted outer sphere mechanism for the dehydrogenation of alcohols.
- Maji, Milan,Chakrabarti, Kaushik,Panja, Dibyajyoti,Kundu, Sabuj
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- Manganese(III) Porphyrin-Catalyzed Dehydrogenation of Alcohols to form Imines, Tertiary Amines and Quinolines
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Manganese(III) porphyrin chloride complexes have been developed for the first time as catalysts for the acceptorless dehydrogenative coupling of alcohols and amines. The reaction has been applied to the direct synthesis of imines, tertiary amines and quinolines where only hydrogen gas and/or water are formed as the by-product(s). The mechanism is believed to involve the formation of a manganese(III) alkoxide complex which degrades into the aldehyde and a manganese(III) hydride species. The latter reacts with the alcohol to form hydrogen gas and thereby regenerates the alkoxide complex.
- Azizi, Kobra,Akrami, Sedigheh,Madsen, Robert
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p. 6439 - 6446
(2019/04/26)
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- Synthesis and Structures of Arene Ruthenium (II)–NHC Complexes: Efficient Catalytic α-alkylation of ketones via Hydrogen Auto Transfer Reaction
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A panel of six new arene Ru (II)-NHC complexes 2a-f, (NHC?=?1,3-diethyl-(5,6-dimethyl)benzimidazolin-2-ylidene 1a, 1,3-dicyclohexylmethyl-(5,6-dimethyl)benzimidazolin-2-ylidene 1b and 1,3-dibenzyl-(5,6-dimethyl)benzimidazolin-2-ylidene 1c) were synthesized from the transmetallation reaction of Ag-NHC with [(η6-arene)RuCl2]2 and characterized. The ruthenium (II)-NHC complexes 2a-f were developed as effective catalysts for α-alkylation of ketones and synthesis of bioactive quinoline using primary/amino alcohols as coupling partners respectively. The reactions were performed with 0.5?mol% catalyst load in 8?h under aerobic condition and the maximum yield was up to 96%. Besides, the different alkyl wingtips on NHC and arene moieties were studied to differentiate the catalytic robustness of the complexes in the transformations.
- Balamurugan, Gunasekaran,Balaji, Sundarraman,Ramesh, Rengan,Bhuvanesh, Nattamai S.P.
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- Synthesis and structure of arene ruthenium(II) complexes: One-pot catalytic approach to synthesis of bioactive quinolines under mild conditions
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Efficient catalytic one-step synthesis of substituted quinoline derivatives using newly synthesized Ru(II) half-sandwich complexes of the type [Ru(η6-p-cymene)Cl(L)] (L = pyrrole-2-aldehydehydrazones) under mild conditions is described. The synthesized complexes exhibit excellent catalytic activity towards the coupling of 2-amino alcohol with functionalized ketones and secondary alcohols in the optimal conditions and afforded the corresponding quinoline derivatives. The synthetic pathway proceeds with high atom efficiency via a sequence of acceptorless dehydrogenation and condensation steps. The maximum isolated yield of the product obtained was up to 97% using 0.3?mol% of catalyst loading for 5?h. These findings significantly advance the scope of the synthesis of bioactive heterocyclic compounds from readily available starting materials.
- Subramanian, Muthumari,Sundar, Saranya,Rengan, Ramesh
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- Blue-light-promoted carbon-carbon double bond isomerization and its application in the syntheses of quinolines
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A blue-light-promoted carbon-carbon double bond isomerization in the absence of any photoredox catalyst is reported. It provides rapid access to a series of quinolines in good to excellent yields under simple aerobic conditions. The protocol is direct, catalyst-free and operationally convenient.
- Chen, Xinzheng,Qiu, Shuxian,Wang, Sasa,Wang, Huifei,Zhai, Hongbin
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p. 6349 - 6352
(2017/08/10)
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- 2 - (b benzene phosphine base ethyl) - (5, 6, 7, 8 - tetrahydro quinolyl) amine ruthenium complex preparation method and application thereof
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The invention discloses a preparation method and application of 2-(diphenylphosphineethyl)-(5,6,7,8-tetrahydroquinolinyl)amine ruthenium complexes. A ligand 2-(diphenylphosphineethyl)-(5,6,7,8-tetrahydroquinolinyl)amine is firstly prepared, and then reacted with RuHCl(CO)(PPh3)3 and RuCl2(PPh3)3 for preparing a complex 1 and a complex 2 which are different in structure, and then the 2-(diphenylphosphineethyl)-(5,6,7,8-tetrahydroquinolinyl)amine ruthenium complex 1 or complex 2 is used to catalyze a condensation reaction of an amino alcohol and a secondary alcohol or a ketone, so that pyridine and quinoline derivatives are synthesized. The preparation method is simple, good in stability, and the catalyst is high in catalytic activity and has the usage amount only being 0.025% by molar of a substrate. The preparation method is applied to production of pyridine and quinoline derivatives, the method is simple, environmental pollution is small, the yield is high and the cost is low.
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Paragraph 0055; 0056; 0057; 0058; 0059
(2017/06/19)
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- A Versatile Ru(II)-NNP Complex Catalyst for the Synthesis of Multisubstituted Pyrroles and Pyridines
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A pincer-type Ru(II)-NNP complex bearing a pyrazolyl-(NH-PtBu2)-pyridine ligand was synthesized and structurally characterized by NMR, IR, elemental analysis, and X-ray single-crystal crystallographic determinations, which efficiently catalyzed the synthesis of multisubstituted pyrroles and pyridines by means of the reactions of secondary alcohols and β- or γ-amino alcohols through deoxygenation and selective C-N and C-C bond formation. The coupling reactions took place with 0.3 mol % catalyst loading and tolerated diverse functional groups. The present work provides an alternative method to construct highly active transition-metal complex catalysts from readily available ligands.
- Chai, Huining,Wang, Liandi,Liu, Tingting,Yu, Zhengkun
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supporting information
p. 4936 - 4942
(2018/02/07)
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- A Ruthenium Catalyst with Unprecedented Effectiveness for the Coupling Cyclization of - Amino Alcohols and Secondary Alcohols
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The ruthenium complex (8-(2-diphenylphosphinoethyl)aminotrihydroquinolinyl)(carbonyl)(hydrido)ruthenium chloride exhibited extremely high efficiency toward the coupling cyclization of -amino alcohols with secondary alcohols. The corresponding products, pyridine or quinoline derivatives, are obtained in good to high isolated yields. On comparison with literature catalysts whose noble-metal loading with respect to -amino alcohols reached 0.5-1.0 mol % for Ru and a record lowest of 0.04 mol % for Ir, the current catalyst achieves the same efficiency with a loading of 0.025 mol % for Ru. The mechanism of acceptorless dehydrogenative condensation (ADC) was proposed on the basis of DFT calculations; in addition, the reactive intermediates were determined by GC-MS, NMR, and single-crystal X-ray diffraction. The catalytic process is potentially suitable for industrial applications.
- Pan, Bing,Liu, Bo,Yue, Erlin,Liu, Qingbin,Yang, Xinzheng,Wang, Zheng,Sun, Wen-Hua
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p. 1247 - 1253
(2016/02/18)
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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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- New Iridium Catalysts for the Selective Alkylation of Amines by Alcohols under Mild Conditions and for the Synthesis of Quinolines by Acceptor-less Dehydrogenative Condensation
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A novel family of iridium catalysts stabilised by P,N-ligands have been introduced. The ligands are based on imidazo[1,5-b]pyridazin-7-amines and can be synthesised with a broad variety of substitution patterns. The catalysts were synthesised quantitatively from the protonated ligands and a commercially available iridium precursor. The catalysts mediate the alkylation of amines by alcohols under mild conditions (70 °C). In addition, the synthesis of quinolines from secondary or primary alcohols and amino alcohols is reported. This sustainable synthesis proceeds through the liberation of two equivalents of water and two equivalents of dihydrogen. The investigations indicate that catalysts suitable for hydrogen autotransfer or borrowing hydrogen chemistry might also be suitable for acceptor-less dehydrogenative condensation reactions. Your H or mine? A family of catalysts that mediate the alkylation of amines by alcohols under mild conditions are introduced (see scheme; HA=hydrogen autotransfer, BH=borrowing hydrogen, ADC=acceptor-less dehydrogenative condensation). The efficient synthesis of quinolines from alcohols and amino alcohols through the liberation of two equivalents of dihydrogen is also mediated by this catalyst family.
- Ruch, Susanne,Irrgang, Torsten,Kempe, Rhett
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supporting information
p. 13279 - 13285
(2016/02/19)
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- Direct synthesis of pyridines and quinolines by coupling of γ-amino-alcohols with secondary alcohols liberating H2 catalyzed by ruthenium pincer complexes
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A novel, one-step synthesis of substituted pyridine- and quinoline-derivatives was achieved by acceptorless dehydrogenative coupling of γ-aminoalcohols with secondary alcohols. The reaction involves consecutive C-N and C-C bond formation, catalyzed by a bipyridyl-based ruthenium pincer complex with a base.
- Srimani, Dipankar,Ben-David, Yehoshoa,Milstein, David
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supporting information
p. 6632 - 6634
(2013/07/26)
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- Highly enantioselective hydrogenation of quinolines using phosphine-free chiral cationic Ruthenium catalysts: Scope, mechanism, and origin of enantioselectivity
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Asymmetric hydrogenation of quinolines catalyzed by chiral cationic η6-arene-N-tosylethylenediamine-Ru(II) complexes have been investigated. A wide range of quinoline derivatives, including 2-alkylquinolines, 2-arylquinolines, and 2-functionalized and 2,3-disubstituted quinoline derivatives, were efficiently hydrogenated to give 1,2,3,4-tetrahydroquinolines with up to >99% ee and full conversions. This catalytic protocol is applicable to the gram-scale synthesis of some biologically active tetrahydroquinolines, such as (-)-angustureine, and 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline, a key intermediate for the preparation of the antibacterial agent (S)-flumequine. The catalytic pathway of this reaction has been investigated in detail using a combination of stoichiometric reaction, intermediate characterization, and isotope labeling patterns. The evidence obtained from these experiments revealed that quinoline is reduced via an ionic and cascade reaction pathway, including 1,4-hydride addition, isomerization, and 1,2-hydride addition, and hydrogen addition undergoes a stepwise H+/H- transfer process outside the coordination sphere rather than a concerted mechanism. In addition, DFT calculations indicate that the enantioselectivity originates from the CH/π attraction between the η6-arene ligand in the Ru-complex and the fused phenyl ring of dihydroquinoline via a 10-membered ring transition state with the participation of TfO- anion.
- Wang, Tianli,Zhuo, Lian-Gang,Li, Zhiwei,Chen, Fei,Ding, Ziyuan,He, Yanmei,Fan, Qing-Hua,Xiang, Junfeng,Yu, Zhi-Xiang,Chan, Albert S. C.
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supporting information; experimental part
p. 9878 - 9891
(2011/08/10)
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- An improved synthesis of quinolines from β-bromovinyl aldehydes and primary arylamines in the presence of a palladium catalyst
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β-Bromovinyl aldehydes are effectively cyclized with primary arylamines in DMF at 110 °C in the presence of a catalytic amount of a palladium catalyst to give the corresponding quinolines in high yields. Copyright
- Sik Cho, Chan,Bo Kim, Hyo,Ren, Wen Xiu,Yoon, Nam Sik
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experimental part
p. 817 - 820
(2011/06/22)
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- Synthesis of quinolines from amino alcohol and ketones catalyzed by [IrCl(cod)]2 or IrCl3 under solvent-free conditions
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2-Aminobenzyl alcohol reacted with 2 equiv amount of ketones under the influence of [IrCl(cod)]2 or IrCl3 and KOH without any solvent, giving the corresponding quinoline derivatives in good yields.
- Taguchi, Kazuhiko,Sakaguchi, Satoshi,Ishii, Yasutaka
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p. 4539 - 4542
(2007/10/03)
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- Synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phenanthridinones via palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitroarenes with β-halo-enals, -enones, or -esters
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Palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitrobenzene (1 R = H) and its derivatives with a range of β-halo-enals, -enones, or -esters readily affords the corresponding β-aryl derivatives, which are converted into the corresponding quinolines, 2-quinolones, phenanthridines, or 6(5H)-phenanthridinones on reaction with dihydrogen in the presence of Pd on C or with TiCl3 in aqueous acetone.
- Banwell, Martin G.,Lupton, David W.,Ma, Xinghua,Renner, Jens,Sydnes, Magne O.
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p. 2741 - 2744
(2007/10/03)
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- Photocyclization of benzalcycloalkanone oximes. A photoannulation route to quinolines
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Photolysis of benzalcycloalkanone oxime derivatives in acidic methanol produces quinoline derivatives in good yields. A three step quinoline annulation of cyclic ketones is described.
- Olsen
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p. 5235 - 5238
(2007/10/02)
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