- Palladium-catalyzed external-oxidant-free coupling reactions between isoquinoline/quinoline N-oxides with olefins
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A convenient and efficient approach for the synthesis of 1-alkenylisoquinolines and 2-alkenylquinolines was developed via palladium-catalyzed coupling reactions between isoquinoline/quinoline N-oxides with olefins under external-oxidant-free conditions. B
- Guo, Tao,Liu, Yu,Zhao, Yun-Hui,Zhang, Pan-Ke,Han, Shu-Lei,Liu, Hong-Min
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- Manganese catalyzed C-alkylation of methylN-heteroarenes with primary alcohols
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C-Alkylations of nine different classes of methyl-substitutedN-heteroarenes, including quinolines, quinoxalines, benzimidazoles, benzoxazoles, pyrazines, pyrimidines, pyridazines, pyridines, and triazines are disclosed. A bench stable earth-abundant Mn(i)-complex catalyzed the chemoselective hydrogen-transfer reaction utilizing a diverse range of primary alcohols as the non-fossil fuel-derived carbon source. The diversifiedN-heteroarenes (41 examples) were isolated in high yields and selectivities. Water is produced as the sole byproduct, making the protocol environmentally benign.
- Jana, Akash,Kumar, Amol,Maji, Biplab
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supporting information
p. 3026 - 3029
(2021/03/29)
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- Role of Benzylic Deprotonation in Nickel-Catalyzed Benzylic Dehydrogenation
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Alkylarenes are readily functionalized via the corresponding benzylic anions. Benzylic anions have been used for a range of catalytic reactions, including Ni-catalyzed dehydrogenation. Interestingly, the employment of Zn(TMP) 2for slow and incomplete deprotonation of the benzylic position was observed. This manuscript describes a preliminary investigation into the deprotonation of heteroarenes and its relationship to Ni-catalyzed benzylic dehydrogenation.
- Zhang, Pengpeng,Cantrell, Rachel L.,Newhouse, Timothy R.
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supporting information
p. 1652 - 1656
(2021/07/31)
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- Iron complex containing diphosphine meta-position carborane ligand as well as preparation method and application of same
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The invention relates to an iron complex containing a diphosphine meta-position carborane ligand as well as a preparation method and application of the same. The iron complex is prepared by the following method: reacting n-BuLi with m-carborane m-C2B10H12, then adding halogenated phosphine for continuous reaction, then adding FeCl2 into a reaction system for continuous reaction, after the reactionis finished, separating the reaction product to obtain an iron complex containing a diphosphine m-carborane ligand, and applying the iron complex to catalytic synthesis of a trans-2-alkenyl azaarenecompound. Compared with the prior art, the method shows efficient catalytic activity in synthesis of the trans-2-alkenyl aza-aromatic hydrocarbon compound through direct condensation reaction of 2-methyl aza-aromatic hydrocarbon and aromatic aldehyde, is low in catalyst dosage, mild in reaction condition, high in reaction rate and relatively high in yield, and has a wide application prospect in industry.
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Paragraph 0032; 0036-0039; 0053-0057
(2020/10/14)
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- Copper-catalyzed asymmetric silyl addition to alkenyl-substituted N -heteroarenes
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Asymmetric conjugate addition of PhMe2SiBPin to a wide range of N-heteroaryl alkenes proceeded in the presence of a copper catalyst coordinated with an easily accessible chiral phosphoramidite ligand to afford useful β-silyl N-heteroarenes in high yields (up to 96%) and excellent enantioselectivities (up to 97% ee).
- Zeng, Ya-Li,Chen, Bo,Wang, Ya-Ting,He, Cheng-Yu,Mu, Zi-Yuan,Du, Ji-Yuan,He, Long,Chu, Wen-Dao,Liu, Quan-Zhong
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supporting information
p. 1693 - 1696
(2020/02/20)
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- Nickel-Catalyzed Dehydrogenation of N-Heterocycles Using Molecular Oxygen
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Herein, an efficient and selective nickel-catalyzed dehydrogenation of five- and six-membered N-heterocycles is presented. The transformation occurs in the presence of alkyl, alkoxy, chloro, free hydroxyl and primary amine, internal and terminal olefin, trifluoromethyl, and ester functional groups. Synthesis of an important ligand and the antimalarial drug quinine is demonstrated. Mechanistic studies revealed that the cyclic imine serves as the key intermediate for this stepwise transformation.
- Banerjee, Debasis,Bera, Atanu,Bera, Sourajit
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supporting information
(2020/09/02)
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- Alkenylation or alkylation reaction method of alkyl-substituted aza-aromatic hydrocarbon
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The invention discloses an alkenylation or alkylation reaction method of alkyl-substituted aza-aromatic hydrocarbon. According to the method, alkyl-substituted aza-aromatic hydrocarbon is used as a starting raw material, alcohol is used as an alkenylation or alkylation reagent, alkali is used as an accelerant, a nitrogen-containing or phosphine-containing ligand is used as an auxiliary agent, andan alkenylation or alkylation product is obtained under a heating condition. The method avoids the use of a transition metal catalyst, and has the advantages of easily available raw materials, simpleoperation, mild synthesis reaction conditions, high reaction efficiency, functional group diversity and the like.
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Paragraph 0024-0034
(2020/07/02)
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- Iron-catalysed alkylation of 2-methyl and 4-methyl azaarenes with alcoholsviaC-H bond activation
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The first Fe-catalysed alkylation of 2-methyl and 4-methyl-azaarenes with a series of alkyl and hetero-aryl alcohols is reported (>39 examples and up to 95% yield). Multi-functionalisation of pyrazines and synthesis of anti-malarial drug (±) Angustureine significantly broaden the scope of this methodology. Preliminary mechanistic investigation, deuterium labeling and kinetic experiments including trapping of the enamine intermediate1a'are of special importance.
- Banerjee, Debasis,Bera, Sourajit,Kabadwal, Lalit Mohan
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supporting information
p. 4777 - 4780
(2020/05/13)
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- Cobalt-catalyzed alkylation of methyl-substituted N-heteroarenes with primary alcohols: Direct access to functionalized N-heteroaromatics
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Phosphine free, air and moisture stable Co(NNN) complex catalyzed alkylation of various methyl-substituted N-heteroarenes with alcohols is reported. Following the borrowing hydrogen methodology, a variety of methyl-substituted N-heteroarenes can be functionalized efficiently. To understand the mechanism of this reaction various kinetic and control experiments were carried out.
- Mishra, Anju,Dwivedi, Ambikesh D.,Shee, Sujan,Kundu, Sabuj
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supporting information
p. 249 - 252
(2019/12/30)
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- AIE fluorescence compound used for detecting viscosity and production and application thereof
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The invention relates to an AIE fluorescence compound used for detecting the viscosity and production and application thereof. The principle of a fluorescent probe of quantitative fluorescence detection of the viscosity is that after the viscosity is impr
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Paragraph 0026-0028
(2019/10/01)
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- Nickel-catalysed alkylation of C(sp3)-H bonds with alcohols: direct access to functionalised N-heteroaromatics
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The first base-metal catalysed coupling of primary alcohols with methyl-N-heteroaromatics is reported. The use of an earth abundant and nonprecious NiBr2/L1 system enables access to a series of C(sp3)-alkylated N-heteroaromatics. Mechanistic studies have established the participation of a hydrogen-borrowing strategy for α-alkylation.
- Vellakkaran, Mari,Das, Jagadish,Bera, Sourajit,Banerjee, Debasis
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supporting information
p. 12369 - 12372
(2018/11/20)
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- Modular o-quinone catalyst system for dehydrogenation of tetrahydroquinolines under ambient conditions
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Quinolines are common pharmacophores present in numerous FDA-approved pharmaceuticals and other bioactive compounds. Here, we report the design and development of new o-quinone-based catalysts for the oxidative dehydrogenation of tetrahydroquinolines to afford quinolines. Use of a Co(salophen) cocatalyst allows the reaction to proceed efficiently with ambient air at room temperature. The utility of the catalytic method is demonstrated in the preparation of a number of medicinally relevant quinolines.
- Wendlandt, Alison E.,Stahl, Shannon S.
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supporting information
p. 11910 - 11913
(2014/10/16)
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- Alkylation of 2-methylquinoline with alcohols under additive-free conditions by Al2O3-supported Pt catalyst
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Supported metal nanoparticle catalysts are studied for alkylation of 2-methylquinoline with benzyl alcohol under additive-free conditions in N 2 atmosphere. Among various metal-loaded Al2O3 catalysts and supported Pt catal
- Chaudhari, Chandan,Hakim Siddiki,Shimizu, Ken-Ichi
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supporting information
p. 6490 - 6493
(2013/11/19)
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- Iridium-catalyzed alkylation of methylquinolines with alcohols
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Iridium-catalyzed alkylation of methylquinolines at the methyl substituent was achieved using alcohols as alkylating agents. The reaction proceeded through a transfer hydrogenation pathway from the alcohol to the Ir complex, affording an aldehyde and Ir-H species, followed by base-assisted aldol condensation and hydrogenation. This method provides an atom-economical and convenient route to alkylquinolines from easily accessible methylquinolines.
- Obora, Yasushi,Ogawa, Shinji,Yamamoto, Nobuyuki
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p. 9429 - 9433,5
(2012/12/12)
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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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- A general protocol for the solvent- and catalyst-free synthesis of 2-styrylquinolines under focused microwave irradiation
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Focused microwave irradiation promoted the very efficient synthesis of 2-styrylquinolines by reaction between quinaldines and benzaldehydes or cinnamaldehydes in the presence of acetic anhydride. Georg Thieme Verlag Stuttgart · New York.
- Staderini, Matteo,Cabezas, Nieves,Bolognesi, Maria Laura,Menendez, J. Carlos
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supporting information; experimental part
p. 2577 - 2579
(2011/12/04)
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- Synthesis and structure of styryl-substituted azines
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New photochromic derivatives of 2-styrylquinoline and 2-styrylquinoxaline were obtained by the condensation of the methyl derivatives of the mentioned heterocycles with substituted benzaldehydes in the presence of basic and acidic catalysts, and also unde
- Gulakova,Sitin,Kuz'Mina,Fedorova
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experimental part
p. 245 - 252
(2011/05/03)
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- Convenient, two-step synthesis of 2-styrylquinolines: an application of the CAN-catalyzed vinylogous type-II Povarov reaction
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A new, experimentally simple, synthesis of 2-styrylquinolines was developed using a two-step sequence based on a CAN-catalyzed three-component type-II vinylogous Povarov reaction from arylamines, cinnamaldehydes, and electron-rich cyclic and noncyclic vin
- Sridharan, Vellaisamy,Avenda?o, Carmen,Carlos Menéndez
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experimental part
p. 2087 - 2096
(2009/07/18)
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- BISPYRIDYL- AND BISQUINOLYLMETHANES. NMR-BASED CHARGE MAPPING OF THE CARBANIONS AND METAL LIGAND PROPERTIES
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Nmr evidence is obtained for mixtures of geometrical stereoisomers of carbanions in DMSO solution of bis(4-)- and bis(2-pyridyl)methane (1) and (2), bis(2-pyridyl)acetonitrile (3), and bis(2-quinolyl)methane (4).When incorporated into ?-charge/shift relat
- Abbotto, Alessandro,Bradamante, Silvia,Pagani, Giorgio A.,Rzepa, Henry,Stoppa, Federica
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p. 757 - 776
(2007/10/02)
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- AN ALDOL-TYPE REACTION OF ACTIVE METHYL GROUPS OF NITROGEN-CONTAINING HETEROAROMATIC COMPOUNDS
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Active methyl groups of nitrogen-containing heteroaromatic compounds react with benzaldehydes in the presence of 9-BBN triflate and diisopropylethylamine in dichloromethane to give the corresponding aldol-type products under mild conditions.
- Hamana, Hiroshi,Sugasawa, Tsutomu
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p. 333 - 336
(2007/10/02)
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