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Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer
A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.
Wu, Cunluo,Bian, Qilong,Ding, Tao,Tang, Mingming,Zhang, Wenkai,Xu, Yuanqing,Liu, Baoying,Xu, Hao,Li, Hai-Bei,Fu, Hua
p. 9561 - 9568
(2021/08/06)

Method for realizing oxidative dehydrogenation of nitrogen-containing heterocyclic ring by using biomass-based carbon material
The invention provides a method for realizing oxidative dehydrogenation of a nitrogen-containing heterocyclic ring by using a biomass-based carbon material, and belongs to the field of organic synthesis. According to the method, the raw materials of the biomass-based carbon material comprise wheat, sorghum, rice, corn straw, wheat straw, peanut shells, sesame shells, bean shells and the like, and are crushed and then ground into powder, the powder is fully mixed with an inorganic alkali, and calcination is performed in an inert gas atmosphere to prepare the biomass-based carbon material; and by using air as an oxygen source, at a temperature of 50-120 DEG C, oxidative dehydrogenation of nitrogen-containing heterocyclic compounds to synthesize quinoline compounds, isoquinoline compounds, acridine compounds, quinazoline compounds, indole compounds, imine compounds, and even quinoline compounds with pharmaceutical activity can be achieved. According to the present invention, easily available wheat flour is adopted as a raw material to prepare a non-metal catalyst, the alkali is not added during the reaction process, and a remarkable industrial application prospect is achieved.
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Paragraph 0010-0011; 0028-0029

(2021/06/26)

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents
Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).
An, Ju Hyeon,Kim, Kyu Dong,Lee, Jun Hee
supporting information
p. 2876 - 2894
(2021/02/01)

Visible-Light-Promoted Efficient Aerobic Dehydrogenation of N-Heterocycles by a Tiny Organic Semiconductor Under Ambient Conditions
An efficient reusable catalytic system has been developed based on perylene diimide (PDI) organic semiconductor for the aerobic dehydrogenation of N-heterocycles with visible light. This practical catalytic system without any additives proceeds under ambient conditions. The minute aggregates of PDI molecules on the surface of SiO2 nanospheres form tiny organic semiconductors, resulting in high-efficiency photo-oxidative activity. Notably, the robustness of this method is demonstrated by the synthesis of a wide range of N-heteroarenes, gram-scale experiments as well as reusability tests.
Su, Chenliang,Yu, Kunyi,Zhang, Hanjie,Zhu, Yongfa
supporting information
p. 1956 - 1960
(2020/04/10)

Metal–Organic Frameworks for the Exploitation of Distance between Active Sites in Efficient Photocatalysis
Discoveries of the accurate spatial arrangement of active sites in biological systems and cooperation between them for high catalytic efficiency are two major events in biology. However, precise tuning of these aspects is largely missing in the design of artificial catalysts. Here, a series of metal–organic frameworks (MOFs) were used, not only to overcome the limit of distance between active sites in bio-systems, but also to unveil the critical role of this distance for efficient catalysis. A linear correlation was established between photocatalytic activity and the reciprocal of inter active-site distance; a smaller distance led to higher activity. Vacancies created at selected crystallographic positions of MOFs promoted their photocatalytic efficiency. MOF-525-J33 with 15.6 ? inter active-site distance and 33 % vacancies exhibited unprecedented high turnover frequency of 29.5 h?1 in visible-light-driven acceptorless dehydrogenation of tetrahydroquinoline at room temperature.
Deng, Hexiang,Gong, Xuan,Jiang, Zhuo,Lu, Lingxiang,Shu, Yufei,Wang, Chao,Xu, Xiaohui
supporting information
p. 5326 - 5331
(2020/02/18)

Nitrogen-coordinated cobalt nanocrystals for oxidative dehydrogenation and hydrogenation of N-heterocycles
To endow non-noble metals with the high catalytic activity that is typically exhibited by noble metals is the central yet challenging aim for substituting noble metals. In this regard, by exploiting the coordination effect of nitrogen, we prepared cobalt nanocrystals stabilized by nitrogen-doped graphitized carbon (Co NCs/N-C). The obtained Co NC/N-C catalyst showed extraordinary performances toward both oxidative dehydrogenation of N-heterocycles and its reverse hydrogenation process under extremely mild conditions. A nearly quantitative conversion could be achieved for oxidative dehydrogenation even at room temperature (25 °C), for which the coordination effect of nitrogen is responsible: the interaction of Co-N induces a partial positive charge on the Co surface, thereby promoting the reaction. In contrast, cobalt nanocrystals supported by pristine carbon (Co NCs/C) proved to be inactive for oxidative dehydrogenation, owing to the lack of nitrogen. Moreover, in Co NCs/N-C, the N-doped graphitized carbon formed a protective layer for Co NCs, which preserved the active valence of Co species and prevented the catalyst from leaching. It was found that the catalyst still retained its excellent catalytic activity after five regeneration cycles; in comparison, its cobaltous oxide counterpart (CoOx/N-C) was barely active. As for the mechanism, electron paramagnetic resonance (EPR) analysis revealed the formation of superoxide anion radicals during the dehydrogenation process. Interestingly, the pressure of feed hydrogen had little effect on the hydrogenation process. Our Co NC/N-C catalyst is capable of activating molecular oxygen and hydrogen as effectively as noble metals; the coordination effect of nitrogen and the protection by the carbon layer in combination confer tremendous potential on the Co NCs/N-C for substituting noble-metal-based catalysts and soluble catalysts for homogeneous reactions.
Wu, Yue,Chen, Zheng,Cheong, Weng-Chon,Zhang, Chao,Zheng, Lirong,Yan, Wensheng,Yu, Rong,Chen, Chen,Li, Yadong
p. 5345 - 5352
(2019/05/29)

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)

Method for preparing quinoline derivative by catalyzing oxidative dehydrogenation of nitrogen-containing heterocyclic ring through carbon nitride material
The invention belongs to the field of chemical synthesis, and particularly relates to a method for preparing a quinoline derivative by catalyzing oxidative dehydrogenation of a nitrogen-containing heterocyclic ring through a carbon nitride material. The carbon nitride material is prepared by using a nitrogen-containing organic macrocyclic compound as a precursor and calcining in an inert atmosphere. During a reaction, oxygen or air is used as an oxidant, and in the presence or absence of a solvent, the reaction is performed at 50-120 DEG C and the carbon nitrogen material can convert the nitrogen-containing heterocyclic ring into the corresponding quinoline derivative. According to the invention, no metal is introduced into a reaction system, and the method is easy to amplify; after being recycled for at least 9 times, a catalyst still maintain good selectivity and activity; therefore, the method has a significant practical prospect during industrial production.
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Paragraph 0018; 0019

(2017/08/29)

Synthesis and Characterization of Iron-Nitrogen-Doped Graphene/Core-Shell Catalysts: Efficient Oxidative Dehydrogenation of N-Heterocycles
An important goal for nanocatalysis is the development of flexible and efficient methods for preparing active and stable core-shell catalysts. In this respect, we present the synthesis and characterization of iron oxides surrounded by nitrogen-doped-graphene shells immobilized on carbon support (labeled FeOx@NGr-C). Active catalytic materials are obtained in a simple, scalable and two-step method via pyrolysis of iron acetate and phenanthroline and subsequent selective leaching. The optimized FeOx@NGr-C catalyst showed high activity in oxidative dehydrogenations of several N-heterocycles. The utility of this benign methodology is demonstrated by the synthesis of pharmaceutically relevant quinolines. In addition, mechanistic studies prove that the reaction progresses via superoxide radical anions (·O2-).
Cui, Xinjiang,Li, Yuehui,Bachmann, Stephan,Scalone, Michelangelo,Surkus, Annette-Enrica,Junge, Kathrin,Topf, Christoph,Beller, Matthias
supporting information
p. 10652 - 10658
(2015/09/28)

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)

Copper nanoparticles from copper aluminum hydrotalcite: An efficient catalyst for acceptor- and oxidant-free dehydrogenation of amines and alcohols
An efficient and simple process for the preparation of stable nanocopper(0) on alumina [Cu(0)/Al2O3] from the inorganic composite precursor copper aluminum hydrotalcite (Cu-AlHT) by a chemical reduction method is described. Cu(0)/ Al2O3 was employed as an efficient catalyst in the acceptor- and oxidant-free dehydrogenation of various amines and alcohols to their corresponding dehydrogenated products in good to excellent yields. The stability of Cu(0)/Al2O3 was assessed by studying its recoverability and reusability in the dehydrogenation of amines and alcohols for up to five cycles.
Damodara, Dandu,Arundhathi, Racha,Likhar, Pravin R.
supporting information
p. 189 - 198
(2014/03/21)

Copper MOF: Scope and limitation in catalytic hydroxylation and nitration of aryl halides
The potential catalytic application of MOFs like [Cu3(btc) 2] (btc=1,3,5-benzenetricarboxylate), [Cu(bdc)] (bdc=1,4- benzenedicarboxylate), [Cu(pymo)2] (pymo=2-hydroxypyrimidinalote) and [Cu(im)2] (im=imidazolate) was explored in the hydroxylation and nitration of aryl halides. Cu3(btc)2 was found to be superior for both the reactions furnishing good to excellent yields of the respective products. The studies demonstrated that MOFs are not recyclable, attributable to their instability in the highly polar and basic conditions demanded for these reactions. Complete transformation of MOFs to copper oxide nanoparticles occurred in hydroxylation, whereas significant alteration in frameworks was observed for the recovered catalyst in nitration.
Priyadarshini,Amal Joseph,Kantam, M. Lakshmi,Sreedhar
p. 6409 - 6414
(2013/07/26)

Synthesis of quinolines and fused pyridocoumarins from N-propargylanilines or propargylaminocoumarins by catalysis with gold nanoparticles supported on TiO2
[5,6]-Fused pyridocoumarins are prepared under mild conditions in excellent yields through the activation of the triple bond of 6-propargylaminocoumarins by gold nanoparticles supported on TiO2. The analogous reaction of N-propargylanilines with Au/TiO2 or Au/Al2O3 resulted in the formation of quinolines.
Symeonidis, Theodoros S.,Lykakis, Ioannis N.,Litinas, Konstantinos E.
p. 4612 - 4616
(2013/06/26)

Synthesis of nitrogen-containing heterocyclic compounds by photooxidation of aromatic azides
It is shown that the photolysis of certain aromatic azides in the presence of oxygen leads to the formation of nitrogen-containing heterocyclic compounds via a domino reaction sequence.
Chainikova, Ekaterina,Safiullin, Rustam,Spirikhin, Leonid,Erastov, Alexey
p. 2140 - 2142
(2013/06/26)

Copper catalyzed ipso-nitration of iodoarenes, bromoarenes and heterocyclic haloarenes under ligand-free conditions
A catalytic protocol for the conversion of haloarenes into the corresponding nitroarenes is presented using copper salts under ligand-free conditions. The method was effectively utilized for the ipso-nitration of a broad variety of haloarenes that includes iodoarenes, bromoarenes, and heterocyclic haloarenes.
Amal Joseph,Priyadarshini,Lakshmi Kantam,Maheswaran
supporting information; experimental part
p. 1511 - 1513
(2012/03/27)

Products of 6-azidoquinoline photooxidation: Thermal and photochemical routes of nitroso oxide consumption
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Chainikov,Safiullin,Teregulova,Spirikhin,Galkin
scheme or table
p. 30 - 33
(2012/08/14)

LIGANDS FOR TRANSITION-METAL-CATALYZED CROSS-COUPLINGS, AND METHODS OF USE THEREOF
Ligands for transition metals are disclosed herein, which may be used in various transition-metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The disclosed methods provide improvements in many features of the transition-metal-catalyzed reactions, including the range of suitable substrates, number of catalyst turnovers, reaction conditions, and efficiency. For example, improvements have been realized in transition-metal-catalyzed cross-coupling reactions.
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Page/Page column 144-145

(2009/07/17)

Pd-catalyzed conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics
(Chemical Equation Presented) An efficient Pd catalyst for the transformation of aryl chlorides, triflates, and nonaflates to nitroaromatics has been developed. This reaction proceeds under weakly basic conditions and displays a broad scope and excellent
Fors, Brett P.,Buchwald, Stephen L.
supporting information; experimental part
p. 12898 - 12899
(2009/12/07)

A practical route to quinolines from anilines
A practical route to quinoline from anilines through acid-mediated cyclization of 3-(N-aryl-N-sulfonylamino)propionaldehydes has been developed. Treatment of the cyclization products, dihydroquinoline intermediates with KOH in DMSO leads to substituted quinolines.
Tokuyama, Hidetoshi,Sato, Masashi,Ueda, Toshihiro,Fukuyama, Tohru
p. 105 - 108
(2007/10/03)

Aromatic nucleophilic substitution of hydrogen: Mechanism of reaction of 6-nitroquinoline with cyanide ions, with and without participation of methyl cyanoacetate
The mechanism of nucleophilic substitution of hydrogen (SNArH) in 6-nitroquinoline 1 by action of cyanide ion in the presence or in the absence of methyl cyanoacetate in dimethyl sulfoxide has been studied by means of 1H NMR. The main reaction products and some side products have been identified and their time-concentration dependences have been determined. An experiment with 13C enriched potassium cyanide proved that the cyano group replaces hydrogen at the 5-position of the starting compound 1. The two main products obtained from the reaction mixture of 6-nitroquinoline 1 and potassium cyanide are 6-hydroxyquinoline-5-carbonitrile 11 and 6,6′-azoquinoline-5,5′-dicarbonitrile 13. On the basis of the data obtained, a mechanism has been suggested for aromatic nucleophilic substitution of hydrogen by cyanide ion in 6-nitroquinoline 1 involving a Meisenheimer adduct of 6-nitroquinoline 1 with cyanide ion and 6-nitrosoquinoline-5-carbonitrile 14 as unstable intermediates.
Halama, Ales,Kavalek, Jaromir,Machacek, Vladimir,Weidlich, Tomas
p. 1839 - 1845
(2007/10/03)

Substituent effects in the hydrolysis of quinoline-boranes
Rates of hydrolysis of quinoline-boranes (QB) in aqueous dioxane are dramatically influenced by substitution in both the hetero and all-carbon ring systems. Effects of 3-, 4-, and 6-substituents appear to be due to electronic induction. Rates obtained at 25 °C with 3- and 4-substituted quinoline-boranes correlate with Hammett σm and σp parameters for both acid-independent and acid-catalyzed pathways, which are depicted respectively by k1 and k2 in the expression -d[QB]/dt = [QB](k1 + k2[H+]). Results are consistent with previously proposed mechanisms involving, for the first-order process, dissociative loss of BH3 and, for the acid-catalyzed reaction, electrophilic displacement of BH3 via cis attack of hydrogen ion at nitrogen. Methyl substitution at C-2 enhances k1 presumably through a steric effect and k2 through an inductive effect. A significant steric effect of the peri hydrogen at C-8 is suggested through a comparison of kinetic parameters for substituted quinoline-boranes with those of isoquinoline-borane, wherein k1 may be observed to change by over 4 orders of magnitude. Such substituent effects are significant in the projected synthetic use of heteroaromatic amine-boranes in protic media.
Minter, David E.,Kelly, Curtis R.,Kelly, Henry C.
p. 3291 - 3294
(2008/10/08)

Condensed Heterocyclics: Part XV - Synthesis and Oxidation Reactions of 1,2,5-Thiadiazoloquinoline
1,2,5-Thiadiazoloquinoline (III) has been synthesised by the reaction of thionyl chloride with 5,6-diaminoquinoline.Its reactions have been studied and the various products isolated have been characterised by elemental analyses, IR and PMR data.
Sharma, K. S.,Kumari, Sharda,Singh, Ram Phul
p. 744 - 746
(2007/10/02)