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Ruthenium-Catalyzed Dehydrogenation Through an Intermolecular Hydrogen Atom Transfer Mechanism
The direct dehydrogenation of alkanes is among the most efficient ways to access valuable alkene products. Although several catalysts have been designed to promote this transformation, they have unfortunately found limited applications in fine chemical synthesis. Here, we report a conceptually novel strategy for the catalytic, intermolecular dehydrogenation of alkanes using a ruthenium catalyst. The combination of a redox-active ligand and a sterically hindered aryl radical intermediate has unleashed this novel strategy. Importantly, mechanistic investigations have been performed to provide a conceptual framework for the further development of this new catalytic dehydrogenation system.
Huang, Lin,Bismuto, Alessandro,Rath, Simon A.,Trapp, Nils,Morandi, Bill
supporting information
p. 7290 - 7296
(2021/03/01)

Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source
Methylation of organohalides represents a valuable transformation, but typically requires harsh reaction conditions or reagents. We report a radical approach for the methylation of (hetero)aryl chlorides using nickel/photoredox catalysis wherein trimethyl orthoformate, a common laboratory solvent, serves as a methyl source. This method permits methylation of (hetero)aryl chlorides and acyl chlorides at an early and late stage with broad functional group compatibility. Mechanistic investigations indicate that trimethyl orthoformate serves as a source of methyl radical via β-scission from a tertiary radical generated upon chlorine-mediated hydrogen atom transfer.
Kariofillis, Stavros K.,Shields, Benjamin J.,Tekle-Smith, Makeda A.,Zacuto, Michael J.,Doyle, Abigail G.
supporting information
p. 7683 - 7689
(2020/04/22)

Superhydrophobic nickel/carbon core-shell nanocomposites for the hydrogen transfer reactions of nitrobenzene and N-heterocycles
In this work, catalytic hydrogen transfer as an effective, green, convenient and economical strategy is for the first time used to synthesize anilines and N-heterocyclic aromatic compounds from nitrobenzene and N-heterocycles in one step. Nevertheless, how to effectively reduce the possible effects of water on the catalyst by removal of the by-product water, and to further introduce water as the solvent based on green chemistry are still challenges. Since the structures and properties of carbon nanocomposites are easily modified by controllable construction, a one step pyrolysis process is used for controllable construction of micro/nano hierarchical carbon nanocomposites with core-shell structures and magnetic separation performance. Using various characterization methods and model reactions the relationship between the structure of Ni?NCFs (nickel-nitrogen-doped carbon frameworks) and catalytic performance was investigated, and the results show that there is a positive correlation between the catalytic performance and hydrophobicity of catalysts. Besides, the possible catalytically active sites, which are formed by the interaction of pyridinic N and graphitic N in the structure of nitrogen-doped graphene with the surfaces of Ni nanoparticles, should be pivotal to achieving the relatively high catalytic performance of materials. Due to its unique structure, the obtained Ni?NCF-700 catalyst with superhydrophobicity shows extraordinary performances toward the hydrogen transfer reaction of nitrobenzene and N-heterocycles in the aqueous state; meanwhile, it was also found that Ni?NCF-700 still retained its excellent catalytic activity and structural integrity after three cycles. Compared with traditional catalytic systems, our catalytic systems offer a highly effective, green and economical alternative for nitrobenzene and N-heterocycle transformation, and may open up a new avenue for simple construction of structure and activity defined carbon nanocomposite heterogeneous catalysts with superhydrophobicity.
Duan, Zhiying,Liu, Fangfang,Pang, Shaofeng,Su, Qiong,Wang, Yanbin,Xie, Xin,Zhang, Ping,Zhang, Yujing,Zhou, Feng
p. 1996 - 2010
(2020/04/07)

Catalytic Aerobic Dehydrogenatin of N-Heterocycles by N-Hydoxyphthalimide
Catalytic methods for the aerobic dehydrogenation of N-heterocycles are reported. In most cases, indoles are accessed efficiently from indolines using catalytic N-hydroxyphthalimide (NHPI) as the sole additive under air. Further studies revealed an improved catalytic system of NHPI and copper for the preparation of other heteroaromatics, for example quinolines. (Figure presented.).
Chen, Weidong,Tang, Hao,Wang, Weilin,Fu, Qiang,Luo, Junfei
supporting information
p. 3905 - 3911
(2020/08/10)

Method for preparation of quinoline compounds
The invention discloses a green preparation method of quinoline compounds. According to the method, cheap and easily available copper salt and N-hydroxyphthalimide are used as catalysts, oxygen is used as an oxidizing agent, oxidation of tetrahydroquinoline compounds is performed in an organic solvent, and synthesis of quinoline compounds is realized. The method has the advantages of simple reaction operation, low reaction cost, high yield, low metal pollution and the like.
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Paragraph 0052-0054

(2020/11/12)

Potassium tert-Butoxide-Promoted Acceptorless Dehydrogenation of N-Heterocycles
Potassium tert-butoxide-promoted acceptorless dehydrogenation of N-heterocycles was efficiently realized for the generation of N-heteroarenes and hydrogen gas under transition-metal-free conditions. In the presence of KOtBu base, a variety of six- and five-membered N-heterocyclic compounds efficiently underwent acceptorless dehydrogenation to afford the corresponding N-heteroarenes and H2 gas in o-xylene at 140 °C. The present protocol provides a convenient route to aromatic nitrogen-containing compounds and H2 gas. (Figure presented.).
Liu, Tingting,Wu, Kaikai,Wang, Liandi,Yu, Zhengkun
supporting information
p. 3958 - 3964
(2019/08/01)

Pd-Catalyzed Alkylation of (Iso)quinolines and Arenes: 2-Acylpyridine Compounds as Alkylation Reagents
The first Pd-catalyzed alkylation of (iso)quinolines and arenes is reported. The readily available and bench-stable 2-acylpyridine compounds were used as an alkylation reagent to form the structurally versatile alkylated (iso)quinolines and arenes. The method affords a convenient pathway for the introduction of alkyl groups into organic molecules.
Wu, Qingsong,Han, Shuaijun,Ren, Xiaoxiao,Lu, Hongtao,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
supporting information
p. 6345 - 6348
(2018/10/20)

High efficiency microwave-assisted synthesis of quinoline from acrolein diethyl acetal and aniline utilizing Ni/Beta catalyst
A facile and solvent-free microwave-assisted approach to quinoline was developed by utilizing both acrolein diethyl acetal and aniline as reagents, firstly employing Ni/Beta zeolite as mild, ecofriendly and low-cost solid catalyst. As high as 83% yield of quinoline was quickly achieved at a short microwave time. The results indicated that the effect of Ni on Beta zeolite not only significantly promoted conversion of acrolein diethyl acetal to effective intermediate but also dramatically accelerated dehydrogenation rate of tetrahydroquinoline/dihydroquinoline to quinoline.
Li, An,Yang, Zan,Yang, Tao,Luo, Cai-Wu,Chao, Zi-Sheng,Zhou, Cong-Shan
p. 21 - 25
(2018/07/06)

Aerobic oxidative dehydrogenation of N-heterocycles catalyzed by cobalt porphyrin
An efficient catalytic procedure has been developed for the aerobic oxidative dehydrogenation of N-heterocycles by cobalt porphyrin in the absence of any additives. The catalytic system could tolerate various 1,2,3,4-tetrahydroquinoline derivatives and some other N-heterocycles. The corresponding N-heteroaromatics could be obtained in 59–86% yields. The mechanism investigation suggested that the aerobic oxidative dehydrogenation might proceed with imine intermediate through radical paths.
Zhou, Weiyou,Chen, Dongwei,Sun, Fu'an,Qian, Junfeng,He, Mingyang,Chen, Qun
supporting information
p. 949 - 953
(2018/02/09)

Metal-Free Dehydrogenation of N-Heterocycles by Ternary h-BCN Nanosheets with Visible Light
An efficient metal-free catalytic system has been developed based on hexagonal boron carbon nitride (h-BCN) nanosheets for the dehydrogenation of N-heterocycles with visible light; hydrogen gas is released in the process, and thus no proton acceptor is needed. This acceptorless dehydrogenation of hydroquinolines, hydroisoquinolines, and indolines to the corresponding aromatic N-heterocycles occurred in excellent yield under visible-light irradiation at ambient temperature. With h-BCN as the photocatalyst and water as the solvent, this environmentally benign protocol shows broad substitution tolerance and high efficiency.
Zheng, Meifang,Shi, Jiale,Yuan, Tao,Wang, Xinchen
supporting information
p. 5487 - 5491
(2018/04/02)

Electrochemical Acceptorless Dehydrogenation of N-Heterocycles Utilizing TEMPO as Organo-Electrocatalyst
Catalytic acceptorless dehydrogenation (CAD) has been a basically important organic transformation to ubiquitous unsaturated compounds without the usage of a sacrificial hydrogen acceptor. In this work, we successfully developed the first electrochemical acceptorless dehydrogenation (ECAD) of N-heterocycles using TEMPO as the organo-electrocatalyst. We have achieved the catalytic dehydrogenation of N-heterocycles in an anode and the release of H2 in a cathode using an undivided-cell system. A variety of six-membered and five-membered nitrogen-heteroarenes can be synthesized in good yields in this system. In addition, this protocol can also be used in the application of important molecular synthesis. Our electrochemical strategy provides a mild and metal-free route for (hetero)aromatic compounds synthesis via the CAD strategy.
Wu, Yong,Yi, Hong,Lei, Aiwen
p. 1192 - 1196
(2018/02/14)

Synthesis method of quinoline compound
The invention discloses a synthesis method of a quinoline compound. The synthesis method of the quinoline compound comprises the following steps: taking a tetrahydroquinoline compound expressed in formula which is as shown in the description as a raw material, taking boron carbon nitrogen as a photocatalyst, adding a solvent, an oxidant and alkali, reacting under visible light radiation condition at room temperature, and purifying a reaction solution and then obtaining the quinoline compound; boron carbon nitrogen (h-BCNx) is a semiconductor polymer photocatalyst which has response to visible light and is free of metal elements; the semiconductor polymer photocatalyst has the advantages of low cost, high availability, high chemical stability, no toxicity, no harm and appropriate forbidden bandwidth and position of energy band; when the catalyst is applied to organic synthesis, the reaction process is simple to operate; the conditions are mild; the catalysis effect is excellent; the conversion rate can reach 90% or more; the yield of target products can reach 95%. The synthesis method of the quinoline compound is simple in process and low in cost, can meet the requirements of practical production, and has relatively great application potential.
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Paragraph 0025; 0026

(2017/12/04)

Acceptorless Dehydrogenation of N-Heterocycles by Merging Visible-Light Photoredox Catalysis and Cobalt Catalysis
Herein, the first acceptorless dehydrogenation of tetrahydroquinolines (THQs), indolines, and other related N-heterocycles, by merging visible-light photoredox catalysis and cobalt catalysis at ambient temperature, is described. The potential applications to organic transformations and hydrogen-storage materials are demonstrated. Primary mechanistic investigations indicate that the catalytic cycle occurs predominantly by an oxidative quenching pathway.
He, Ke-Han,Tan, Fang-Fang,Zhou, Chao-Zheng,Zhou, Gui-Jiang,Yang, Xiao-Long,Li, Yang
supporting information
p. 3080 - 3084
(2017/03/14)

Method for catalyzing nitrogen heterocyclic ring compound for oxidative dehydrogenation with hydrotalcite-like material
The invention relates to a method for catalyzing a nitrogen heterocyclic ring compound for oxidative dehydrogenation with a hydrotalcite-like material, and belongs to the application aspect of a hydrotalcite-like component. The hydrotalcite-like component can be expressed as: A-MxM-LDHs (A=OH or CO3; M=Ni, Co, Cu, Mg or Zn; M=Fe, Mn, Al; M/M=(2 to 4)). Under existence of the catalyst and without adding any additives, oxidative dehydrogenation reaction is performed on the heterocyclic ring compound under a mild condition to prepare a corresponding aromatic compound. According to the method provided by the invention, the hydrotalcite-like material is based on non-noble metal, can be synthesized largely, and can be recycled; the method has the advantages of being high in catalytic reaction efficiency, mild in reaction condition, low in cost, easy to industrialize and the like.
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Paragraph 0048; 0049; 0050; 0051; 0052

(2017/10/27)

Palladium Nanoparticles Stabilized by Metal–Carbon Covalent Bonds as an Expeditious Catalyst for the Oxidative Dehydrogenation of Nitrogen Heterocycles
The first method for the dehydrogenation of nitrogen heterocycles catalyzed by a palladium nanocatalyst was developed. Carbon–metal covalent-bond-stabilized nanoparticles were found to be efficient for the dehydrogenation process in the presence of tert-butyl hydroperoxide. A variety of N-heterocycles were transformed into functionalized quinolines in medium to excellent yields in water as the solvent under mild conditions by a simple operation.
Sun, Xiao-Tao,Zhu, Jie,Xia, Yun-Tao,Wu, Lei
p. 2463 - 2466
(2017/07/12)

Highly Enantioselective Direct Synthesis of Endocyclic Vicinal Diamines through Chiral Ru(diamine)-Catalyzed Hydrogenation of 2,2′-Bisquinoline Derivatives
An asymmetric hydrogenation of 2,2′-bisquinoline and bisquinoxaline derivatives, catalyzed by chiral cationic ruthenium diamine complexes, was developed. A broad range of chiral endocyclic vicinal diamines were obtained in high yields with excellent diastereo- and enantioselectivity (up to 93:7 dl/meso and >99 % ee). These chiral diamines could be easily transformed into a new class of chiral N-heterocyclic carbenes (NHCs), which are important but difficult to access.
Ma, Wenpeng,Zhang, Jianwei,Xu, Cong,Chen, Fei,He, Yan-Mei,Fan, Qing-Hua
supporting information
p. 12891 - 12894
(2016/10/04)

Axially Chiral Bifunctional 8,8′-Biquinolyl: Synthesis of 7,7′-Dihydroxymethyl-8,8′-biquinolyl via Pd-Catalyzed Double C-H Oxidation of 7,7′-Dimethyl-8,8′-biquinolyl
Bifunctional C2-symmetric 7,7′-dihydroxymethyl-8,8′-biquinolyl (2) was synthesized in short steps via (i) Cu/Pd-catalyzed homo coupling of 7-methyl-8-bromoquinoline and (ii) Pd(II)-catalyzed double C-H oxidation. Axial chirality of 2 and its synthetic precursor 7,7′-dimethyl-8,8′-biquinolyl (3) is stable. Optically active 2 was obtained through separation of racemic 2 by chiral column HPLC or Pd(II)-catalyzed double C-H oxidation of optically active 3. The absolute stereochemistry of enantiomers of 2 and 3 was determined using the exciton chirality method.
Kitamura, Mitsuru,Fukuma, Hiroaki,Kobayashi, Mitsuaki,Okayama, Shinya,Okauchi, Tatsuo
p. 3956 - 3960
(2016/05/24)

Copper-Promoted Tandem Reaction of Azobenzenes with Allyl Bromides via N=N Bond Cleavage for the Regioselective Synthesis of Quinolines
A copper-promoted tandem reaction of a variety of azobenzenes and allyl bromides via N=N bond cleavage to regioselectively construct quinoline derivatives has been developed. The azobenzenes act as not only construction units but also an oxidant for quinoline formation.
Yi, Xiangli,Xi, Chanjuan
supporting information
p. 5836 - 5839
(2015/12/11)

Synthesis of quinolines by iron-catalyzed reaction of anilines with propane-1,3-diol
Quinoline and its derivatives were synthesized by cyclocondensation of anilines with propane-1,3-diol in 57-96% yield in the presence of iron-containing catalysts in carbon tetrachloride.
Khusnutdinov,Bayguzina,Aminov
p. 2725 - 2727
(2016/02/18)

Quinoline synthesis by improved Skraup-Doebner-Von Miller reactions utilizing acrolein diethyl acetal
A robust synthetic method has been developed as an improvement to the venerable Skraup-Doebner-Von Miller reaction providing access to various quinoline products. The straightforward procedure utilizes acrolein diethyl acetal as a three-carbon annulation partner with aniline substrates in a monophasic, organic solvent-free reaction medium. Differentially substituted aniline precursors were found to be compatible with the reaction conditions and the corresponding quinoline products are isolated in moderate to good yields.
Ramann, Ginelle A.,Cowen, Bryan J.
supporting information
p. 6436 - 6439
(2015/11/16)

HOTf-catalyzed intermolecular hydroamination reactions of alkenes and alkynes with anilines
Herein, the intermolecular hydroamination of alkenes and alkynes with anilines catalyzed by HOTf under mild conditions has been developed. This reaction provides one of the simplest alkene and alkyne addition methods and is an alternative to metal-catalyzed reactions. At the same time, the intramolecular hydroamination of alkynes with anilines proceeds smoothly to obtain quinolines. We found that this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.
Xu, Xuefeng,Zhang, Xu,Wang, Zhiqiang,Kong, Manman
p. 40950 - 40952
(2015/05/20)

Quinoline and phenanthroline preparation starting from glycerol via improved microwave-assisted modified Skraup reaction
An efficient "green" modified Skraup reaction in neat water was developed using inexpensive, abundant and environmentally-friendly glycerol under microwave irradiation conditions. Starting from aniline derivatives, various quinolines were obtained in 10-66% yields. The use of nitroaniline led to the corresponding phenanthrolines in 15-52% yields, respectively. This journal is the Partner Organisations 2014.
Saggadi, Hanen,Luart, Denis,Thiebault, Nicolas,Polaert, Isabelle,Estel, Lionel,Len
p. 21456 - 21464
(2014/06/10)

Enantioselective, nickel-catalyzed suzuki cross-coupling of quinolinium ions
Quinolinium ions are engaged in an asymmetric, Ni-catalyzed Suzuki cross-coupling to yield 2-aryl- and 2-heteroaryl-1,2-dihydroquinolines. Key to the development of this method is the use of a Ni(II) precatalyst that activates without the need for strong reductants or high temperatures. The Ni-iminium activation mode is demonstrated as an exceptionally mild pathway to generate enantioenriched products from racemic starting materials.
Shields, Jason D.,Ahneman, Derek T.,Graham, Thomas J. A.,Doyle, Abigail G.
supporting information
p. 142 - 145
(2014/01/23)

Reversible hydrogenation-oxidative dehydrogenation of quinolines over a highly active pt nanowire catalyst under mild conditions
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Ge, Danhua,Hu, Lei,Wang, Jiaqing,Li, Xingming,Qi, Fenqiang,Lu, Jianmei,Cao, Xueqin,Gu, Hongwei
p. 2183 - 2186
(2013/08/23)

Reduction of nitroarenes followed by propanol group transfer from tris(3-hydroxypropyl)- amine and cyclization leading to quinolines under heterogeneous Pd-C catalysis
Nitroarenes having electron-donating or -withdrawing substituents are reduced to anilines and cyclized with tris(3- hydroxypropyl)amine in the presence of a catalytic amount of Pd-C along with tin(II) chloride and isopropanol in dioxane-H2O medium to give the corresponding quinolines in good to excellent yields. Copyright
Cho, Chan Sik,Kim, Tae Gyun,Yoon, Nam Sik
experimental part
p. 291 - 293
(2010/08/04)

Ruthenium-catalyzed synthesis of quinolines via reductive heteroannulation of nitroarenes with 3-amino-1-propanols
Nitroarenes are reductively cyclized with 3-amino-1-propanols in dioxane/H2O in the presence of a ruthenium catalyst and tin(II) chloride dihydrate together with isopropanol to afford the corresponding quinolines. A reaction pathway involving i
Cho, Chan Sik,Kyung Kim, Tae,Kim, Tae-Jeong,Shim, Sang Chul,Yoon, Nam Sik
p. 291 - 294
(2007/10/03)

Synthesis of quinolines by ruthenium-catalyzed heteroannulation of anilines with 3-amino-1-propanol
Anilines react with 3-amino-1-propanol in dioxane in the presence of a catalytic amount of a ruthenium catalyst and tin(II) chloride dihydrate together with a hydrogen acceptor to afford the corresponding quinolines in moderate yields.
Cho, Chan Sik,Oh, Byoung Ho,Shim, Sang Chul
p. 1175 - 1178
(2007/10/03)

BROMINATION OF QUINOLINE DERIVATIVES WITH N-BROMOSUCCINIMIDE. ISOMERIC COMPOSITION OF THE BROMINATION PRODUCTS BY PMR AND GLC
The bromination of quinoline and substituted quinolines with N-bromosuccinimide in concentrated H2SO4 takes place exclusively in the homocyclic part.Bromo-substituted quinolines can be obtained by this method.The bromination products were identified by PMR spectroscopy.The differences among the mono-, di-, and trisubstituted (in the benzene ring) compounds were established on the basis of the type of spectrum of the protons of the homocyclic part of the molecule.The compositions of the reaction mixtures were studied by GLC.
Tochilkin, A. I.,Kovel'man, I. R.,Prokof'ev, E. P.,Gracheva, I. N.,Levinskii, M. V.
p. 892 - 897
(2007/10/02)

FORMATION OF INDOLES AND QUINOLINES BY FLASH VACUUM PYROLYSIS
Flash vacuum pyrolysis of N-(2-methylphenyl)benzimidoyl chlorides and N,N-dimethyl-N'-(2-methylphenyl)formamidines provides a simple route to 2-aryl- and 2-unsubstituted indoles.Pyrolysis of N,N-dimethyl-N-(2-methylphenyl)-acetamidines gives mainly quinolines in a reaction which reveals a novel, high temperature rearrangement of 3,4-dihydroquinolines.
Randles, K. R.,Storr, R. C.
p. 5555 - 5558
(2007/10/02)

The structures of huperzine A and B, two new alkaloids exhibiting marked anticholinesterase activity
Huperzine A and B, two new Lycopodium alkaloids isolated from Huperzia serrata (Thunb.) Trev., are shown to possess structures 1 and 3, respectively, on the basis of chemical and spectroscopic data.
Liu, Jia-Sen,Zhu, Yuan-Long,Yu, Chao-Mei,Zhou, You-Zuo,Han, Yan-Yi,et al.
p. 837 - 840
(2007/10/02)

Selectivity of Hydrogenations. Part 4. 6- and 8-Substituted Quinaldines. Yield of Tetrahydroderivatives and Basicities of Quinolines
Hydrogenation of 6- or 8-R-substituted quinaldines over platinum in trifluoracetic acid gave higher yields (ca.90percent) of 5,6,7,8-tetrahydroderivatives than hydrogenation of the corresponding quinolines.The pKa-values of 20 quinolines and quinaldines were determined by measuring the half-neutralisation potentials in acetic anhydride.More basic quinolines gave higher yields of 5,6,7,8-tetrahydroproduct; exceptions are 6- and 8-methylquinoline and 8-tert. butylquinoline.Explanations for these observations are suggested. - Keywords:Catalytic hydrogenation; PKa-Values; Quinaldines; Quinolines; 5,6,7,8-Tetrahydroquinolines, yields of.
Hoenel, Michael,Vierhapper, Friedrich W.
p. 1219 - 1228
(2007/10/02)

Thermolysis of Polyazapentadienes. Part 7. An Unambiguous Route to 7-Substituted Quinolines from Cinnamaldehyde Derivatives
Flash vacuum pyrolysis of the cinnamaldehyde phenylhydrazone derivatives (4) - (6) or O-alkyl oxime derivatives (7) - (12) at 600 -650 deg C and 10-2 - 10-3 Torr leads to approximately equal quantities of cinnamonitriles and quinolines.Use of a p-substituted cinnamaldehyde derivatives gives the appropriate 7-substituted quinoline in high isomeric purity; the reactions take place via conjugated iminyl radicals.
Hickson, Clare L.,McNab, Hamish
p. 1569 - 1572
(2007/10/02)

Thermolysis of Polyazapentadienes. Part 6. Gas-phase Cyclisation of 1,5-Diaryl-1,5-diazapentadienes: Mechanistic Aspects and some Synthetic Applications
The mode of formation of quinolines by gas-phase pyrolysis of 1,5-diaryl-1,5-diazapentadienes is contrasted with the thermal behaviour of 1,2,5-triazapentadienes.The mechanism involves concerted ring closure followed by a rapid 1,5-hydrogen shift to give a 3,4-dihydroquinoline intermediate, e.g. (19) or (21).Subsequent aromatisation takes place by a stepwise, free-radical process.Methylquinolines (9), (10), (12), and (13) were obtained on a preparative scale by this method.
McNab, Hamish,Murray, M. Elizabeth-Ann
p. 1565 - 1568
(2007/10/02)