cas 119-91-5, 2,2'-Biquinoline | Articles data

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Nickel-Catalyzed Electrochemical Reductive Homocouplings of Aryl and Heteroaryl Halides: A Useful Route to Symmetrical Biaryls
Due to their widespread presence in functional materials and pharmaceuticals, biaryls are of fundamental importance in organic chemistry. Methods for the synthesis of symmetrical biaryls generally involve both metallic reduction and transition-metal catalysis. In this work, we show that electroreduction can also constitute a very relevant way to achieve the nickel-catalyzed reductive synthesis of symmetrical biaryl compounds. Therefore, it is demonstrated that both aryl and heteroaryl halides undergo reductive coupling to furnish the corresponding symmetrical biaryls in fair to excellent yields. Reactions are performed under very mild conditions thus ensuring important functional group tolerance.
Rahil, Rima,Sengmany, Stéphane,Le Gall, Erwan,Léonel, Eric
p. 146 - 154
(2018)
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Heterogenous catalytic method for the synthesis of biquinolines and bipyridines
A method has been developed for the synthesis of 2,2′- and 3,3′-biquinolines and of 4,4′-bipyridine based on the coupling of 2- and 3-bromoquinoline or 4-bromopyridine using a Pd/C-hydrazine-KOH catalytic system.
Aksenov,Goncharov
p. 1491 - 1492
(2008)
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Gershuns,Pustovar
(1971)
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Synthesis and Reaction of 2,2'-Biquinolyl
A title compound is readily prepared from methyl 2-quinolyl sulfoxide (3) with methylmagnesium bromide in excellent yield and an ipso addition of alkylmagnesium halides to 2,2'-biquinolyl (4) is also described.
Wakabayashi, Shoji,Kubo, Yukihiro,Takeda, Takashi,Uenishi, Jun-ichi,Oae, Shigeru
p. 2338 - 2341
(1989)
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Jackson et al.
p. 1126,1127, 1130, 1131
(1963)
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First cross-coupling reactions of arylmagnesates: A convenient access to heteroarylquinolines
2-, 3- and 4-Bromoquinolines were converted to the corresponding lithium tri(quinolyl)magnesates at -10°C on treatment with Bu3MgLi in THF. The resulting organomagnesium derivatives were involved in catalyzed cross-coupling reactions with heteroaryl bromides and chlorides to afford functionalized quinolines.
Dumouchel, Sylvain,Mongin, Florence,Trécourt, Fran?ois,Quéguiner, Guy
p. 3877 - 3880
(2003)
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A [2 + 3] Reductive Cyclodimerization of Quinoline by SmI2
Pyridine and its derivatives are rather difficult to reduce, and the products often undergo a very fast reoxidation to regain aromaticity. The reduction of quinoline by SmI2 results in an instantaneous [2 + 3] cyclization reaction, forming a bridged seven-membered ring within a polycyclic system.
Yella, Ramesh,Gottlieb, Hugo E.,Hoz, Shmaryahu
p. 8929 - 8932
(2015)
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Homocoupling of aryl halides using Nickel(II) complex and zinc in the presence of Et4NI. An efficient method for the synthesis of biaryls and bipyridines
Reduction of NiX2(PPh3)2 with zinc in the presence of Et4NI gives a nickel catalyst which has been proven to be useful for the coupling of aryl halides. This nickel catalyst can be prepared in THF without an additional triphenylphosphine and is effective for the homocoupling of aryl chlorides, bromides, and iodides to produce biaryls and bipyridines in good yields. The reported new approach provides a simple access to novel derivatives of biaryls and bipyridines.
Iyoda,Otsuka,Sato,Nisato,Oda
p. 80 - 87
(1990)
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Synthesis and coordination behaviour of aluminate-based quinolyl ligands
The effects of moving the donor N-atom from the 2-position in lithium (2-pyridyl)- and (2-quinolyl)aluminates to the more remote position in (8-quinolyl)aluminates have been investigated by solid-state structural and DFT computational studies of the new c
Bond, Andrew D.,Colebatch, Annie L.,García-Rodríguez, Raul,Hanf, Schirin,Rincón-Nocito, Marina,Waters, Jessica E.,Wright, Dominic S.
p. 14551 - 14559
(2021)
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Ruthenium(II) Complexes with Three Different Diimine Ligands
The synthesis of tris-heteroleptic complexes of Ru(II) with diimine ligands is descriebed.Ten compounds 2 (R=H, CH3; L=2,2'-bipyridine (bpy), 4,4'-dimethyl-2,2'-bipyridine (Me2bpy), 2,2'-bipyrimidine (bpm), 2,2'-biisoquinoline (bii
Zelewsky, Alex,Gremaud, Gabriel
p. 1108 - 1115
(1988)
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Badr,Aly
p. 3401,3405
(1972)
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Rapoport et al.
p. 372
(1960)
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Sheinkman et al.
(1977)
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Highly Ordered Mesoporous Cobalt Oxide as Heterogeneous Catalyst for Aerobic Oxidative Aromatization of N-Heterocycles
N-heterocycles are key structures for many pharmaceutical intermediates. The synthesis of such units normally is conducted under homogeneous catalytic conditions. Among all methods, aerobic oxidative aromatization is one of the most effective. However, in homogeneous conditions, catalysts are difficult to be recycled. Herein, we report a heterogeneous catalytic strategy with a mesoporous cobalt oxide as catalyst. The developed protocol shows a broad applicability for the synthesis of N-heterocycles (32 examples, up to 99 % yield), and the catalyst presents high turnover numbers (7.41) in the absence of any additives. Such a heterogenous approach can be easily scaled up. Furthermore, the catalyst can be recycled by simply filtration and be reused for at least six times without obvious deactivation. Comparative studies reveal that the high surface area of mesoporous cobalt oxide plays an important role on the catalytic reactivity. The outstanding recycling capacity makes the catalyst industrially practical and sustainable for the synthesis of diverse N-heterocycles.
Cao, Yue,Wu, Yong,Zhang, Yuanteng,Zhou, Jing,Xiao, Wei,Gu, Dong
p. 3679 - 3686
(2021/06/18)

A Mild Method for Electrochemical Reduction of Heterocyclic N-Oxides
Deoxygenation of heteroaromatic N-oxides is commonly accomplished using chemical or enzymatic methods. In this work, we report on an expedient protocol for electrochemical reduction of pyridine N-oxide derivatives under mild conditions. A diverse range of mono- and bis N-oxides were converted into the corresponding nitrogen bases in good yields. Importantly, the method is highly selective towards N-oxides and tolerates challenging halo and nitro substituents in the heteroaromatic ring.
Fukazawa, Yasuaki,Rubtsov, Aleksandr E.,Malkov, Andrei V.
supporting information
p. 3317 - 3319
(2020/05/25)

Copper-Catalyzed ortho-Functionalization of Quinoline N-Oxides with Vinyl Arenes
An efficient copper-catalyzed regioselective C?H alkenylation and borylative alkylation of quinoline N-oxides with vinyl arenes in the presence of pinacol diborane has been developed. The reaction proceeds through the borylcupration of the vinyl arenes followed by nucleophilic attack of the resulting alkyl copper species to the quinoline N-oxides. Benzoquinone and KOtBu were identified as the necessary additives at the second step of the reaction that are crucial for the success of the reaction. A wide range of C2-functionalizaed quinolines were obtained with good functional group tolerance, which may find utilities in pharmaceuticals and synthetic chemistry.
Hu, Hui,Hu, Xiaoping,Liu, Yuanhong
supporting information
p. 18975 - 18979
(2020/08/25)

Dehydrogenative Synthesis of 2,2′-Bipyridyls through Regioselective Pyridine Dimerization
2,2′-Bipyridyls have been utilized as indispensable ligands in metal-catalyzed reactions. The most streamlined approach for the synthesis of 2,2′-bipyridyls is the dehydrogenative dimerization of unfunctionalized pyridine. Herein, we report on the palladium-catalyzed dehydrogenative synthesis of 2,2′-bipyridyl derivatives. The Pd catalysis effectively works with an AgI salt as the oxidant in the presence of pivalic acid. A variety of pyridines regioselectively react at the C2-positions. This dimerization method is applicable for challenging substrates such as sterically hindered 3-substituted pyridines, where the pyridines regioselectively react at the C2-position. This reaction enables the concise synthesis of twisted 3,3′-disubstituted-2,2′-bipyridyls as an underdeveloped class of ligands.
Yamada, Shuya,Kaneda, Takeshi,Steib, Philip,Murakami, Kei,Itami, Kenichiro
supporting information
p. 8341 - 8345
(2019/04/30)

Structural and Synthetic Insights into Pyridine Homocouplings Mediated by a β-Diketiminato Magnesium Amide Complex
The reaction of [(DippNacnac)Mg(TMP)] (1) with 4-subtituted pyridines proceeds via sequential regioselective metallation and 1,2-addition to furnish a range of symmetric 4,4′-R2-2,2′-bipyridines in good yield, representing a new entry into bipyridine synthesis. Interestingly, the reaction of 1 with 2-OMe-pyridine led to formation of asymmetric bipyridine 6, resulting from the C6-magnesiation of the heterocycle followed by a C?C coupling step by addition to the C2 position of a second, non-metallated molecule, and subsequent elimination of [DippNacnacMgOMe]2 (7). Synthesis combined with spectroscopic and structural analysis help rationalise the underlying processes resulting in the observed reactivity, and elucidate the key role that the sterically encumbered β-diketiminate ligand plays in determining regioselectivity.
Davin, Laia,Clegg, William,Kennedy, Alan R.,Probert, Michael R.,McLellan, Ross,Hevia, Eva
supporting information
p. 14830 - 14835
(2018/09/25)

Intramolecular Desulfitative Coupling: Nickel-Catalyzed Transformation of Diaryl Sulfones into Biaryls via Extrusion of SO2
As a new transformation of organosulfur compounds, intramolecular desulfitative coupling of diaryl sulfones to the corresponding biaryls has been developed with the aid of nickel-NHC catalysts. This catalytic elimination of SO2 was also applicable to alkenyl aryl sulfone to furnish the corresponding alkenyl arene.
Takahashi, Fumiya,Nogi, Keisuke,Yorimitsu, Hideki
p. 6601 - 6605
(2018/10/20)

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)

MANUFACTURING METHOD OF BIPYRIDYL COMPOUND
PROBLEM TO BE SOLVED: To provide various bipyridyl compounds by a reaction less in process number with a relief condition and short time. SOLUTION: A compound represented by the general formula, where Y represents a hydrogen atom or a nitrogen atom, R1 represents a cyano group, a halogen atom, an alkyl group which may be substituted, an alkoxy group which may be substituted, an aryl group which may be substituted, a heteroaryl group which may be substituted or a silyl group which may be substituted, n represents an integer of 0 to 4 and 2 R1 binding same benzene ring may bind each other to form a ring when n is 2 or more. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0083; 0100-0102

(2017/09/16)

O-bicyclic amine compounds as well as preparation method and chiral products thereof
The invention relates to the field of asymmetric synthesis methods, and discloses a preparation method of o-bicyclic amine compounds. The method comprises the step of enabling a compound having a structure as shown in a formula (1) and hydrogen to be subjected to an addition reaction in presence of a chiral catalyst, wherein the chiral catalyst is a complex having a structure as shown in a formula (2). The invention also provides chiral products of the o-bicyclic amine compounds prepared by the method, and the o-bicyclic amine compounds. After the method is adopted, the selective hydrogenation reduction of the compound having the structure as shown in the formula (1) is realized by using the hydrogen, so that octahydrogenated products, i.e., the o-bicyclic amine compounds shown in a formula (4) are produced with low cost. The formula (1), the formula (2) and the formula (4) are described in the description.
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(2017/11/04)

Potassium Hydroxide-Catalyzed Alkynylation of Heteroaromatic N-Oxides with Terminal Alkynes
An efficient potassium hydroxide-catalyzed alkynylation of heteroaromatic N-oxides under transition-metal-free conditions with the assistance of visible-light has been developed. Various C2-alkynylheterocycles were obtained in up to 92% yield with good functional group tolerance. This new method is operational simple, highly efficient, atom economic, and environmental friendly. (Figure presented.).
Chen, Xiaopei,Yang, Fangfang,Cui, Xiuling,Wu, Yangjie
supporting information
p. 3922 - 3926
(2017/11/30)

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)

Transition Metal Free Homocoupling of Unactivated Electron Deficient Azaarenes
This work has established the first direct homocoupling of unactivated electron deficient azaarenes in the presence of TMPMgCl (2,2,6,6 tetramethylpiperidinylmagnesium chloride) and TMEDA (tetramethylethylenediamine). In this process, no transition metal was used while freely available air was employed as the oxidant. The investigated successful substrates included quinolines, isoquinoline, 3 phenylated pyridines, and 2 phenylated quinoxalines, giving moderate to high yields. The homocoupling of quinolines was effectively scaled up to one gram in high yield. Additionally, an iridium complex of 6,6′ dimethyl 2,2′ biquinoline was prepared and characterized as an efficient red emitting material.
Xie, Wen Wen,Liu, Yue,Yuan, Rui,Zhao, Dan,Yu, Tian Zhi,Zhang, Jian,Da, Chao Shan
p. 994 - 1002
(2016/04/05)

Method for preparing symmetric dimer of nitrogen heterocyclic ring aromatic compound
The invention discloses a method for preparing a symmetric dimer of a nitrogen heterocyclic ring aromatic compound, a product prepared by the method and application of the product. The method comprises the following steps: adding a solvent in which a Grignard reagent is dissolved into a reaction container under protection of an inert gas, and slowly dropwise adding secondary amine into the Grignard reagent solution; then, adding a second kind of solvent into the reaction container to dissolve the product obtained in the reaction of the Grignard reagent and the secondary amine, adding a nitrogen complex reagent into the mixture, complexing, and adding a nitrogen heterocyclic ring aromatic compound to react at 20-200 DEG C; and quenching the reaction after the reaction is completed, and oxidizing the reaction product with air or oxygen to transform the reaction product into the symmetric dimer of the nitrogen heterocyclic ring aromatic compound. The method does not need transition metal, can be used for reducing production cost and environmental pollution, has an environment-friendly process, and can be used for preparing a series of novel compounds with illumination performance or pharmacological activity.
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Paragraph 0024; 0025; 0026

(2016/10/08)

Mechanistic insights into the potassium: Tert -butoxide-mediated synthesis of N-heterobiaryls
We report herein that symmetrical and non-symmetrical N-heterobiaryls are produced by a potassium tert-butoxide-mediated dimerization of heterocyclic N-oxides. The reaction is scalable and transition metal-free, and can be carried out under thermal and microwave conditions. Preliminary mechanistic studies point to the involvement of radical anionic intermediates arising from the N-oxide substrates and potassium tert-butoxide.
Stephens, David E.,Lakey-Beitia, Johant,Burch, Jessica E.,Arman, Hadi D.,Larionov, Oleg V.
supporting information
p. 9945 - 9948
(2016/08/11)

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
p. 12891 - 12894
(2016/10/04)

Nickel-catalyzed one-pot deoxygenation and reductive homocoupling of phenols via C-O activation using TCT reagent
A new method for C-O bond activation of phenolic compounds has been achieved using 2,4,6-trichloro-1,3,5-triazine to utilize in one-pot Ni-catalyzed deoxygenation and reductive homocoupling reactions. With this simple method, phenolic compounds were converted to their corresponding arenes or biaryl compounds under mild conditions. The introduced methodology has a broad scope and demonstrates good functional group compatibility.
Iranpoor, Nasser,Panahi, Farhad
supporting information
p. 214 - 217
(2015/01/30)

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)

Reductive couplings of 2-halopyridines without external ligand: Phosphine-free nickel-catalyzed synthesis of symmetrical and unsymmetrical 2,2'-bipyridines
An unexpectedly facile synthetic approach for symmetrical and unsymmetrical 2,2'-bipyridines through the Ni-catalyzed reductive couplings of 2-halopyridines was developed. The couplings were efficiently catalyzed by 5 mol % of NiCl2.6H2O without the use of external ligands. A variety of 2,2'-bipyridines including caerulomycin F have been efficiently synthesized.
Liao, Lian-Yan,Kong, Xing-Rui,Duan, Xin-Fang
p. 777 - 782
(2014/04/03)

An electrochemical nickel-catalyzed arylation of 3-amino-6- chloropyridazines
3-Amino-6-aryl- and 3-amino-6-heteroarylpyridazines have been obtained in generally good yield using a nickel-catalyzed electrochemical cross-coupling between 3-amino-6-chloropyridazines and aryl or heteroaryl halides at room temperature. Comparative experiments involving classical palladium-catalyzed reactions, such as Suzuki, Stille, or Negishi cross-couplings, reveal that the electrochemical method can constitute a reliable alternative tool for biaryl formation. A possible reaction mechanism is proposed on the basis of electrochemical analyses.
Sengmany, Stephane,Vitu-Thiebaud, Arnaud,Le Gall, Erwan,Condon, Sylvie,Leonel, Eric,Thobie-Gautier, Christine,Pipelier, Muriel,Lebreton, Jacques,Dubreuil, Didier
p. 370 - 379
(2013/03/13)

Bimetallic gold-palladium alloy nanoclusters: An effective catalyst for Ullmann coupling of chloropyridines under ambient conditions
An efficient method for the Ullmann coupling of chloropyridines catalyzed by poly(N-vinylpyrrolidone) (PVP)-stabilized bimetallic Au-Pd alloy nanoclusters (NCs) under ambient conditions is demonstrated. The reaction does not occur with either gold or palladium single-metal clusters alone, nor with a physical mixture of the two metals. The experimental results indicate that the inclusion of Au as a nearest heteroatom is crucial to initiate the coupling and its composition up to 50% is essential to accelerate the reaction. Unlike the conventional transition metal catalysis, 2-chloropyridine was found to be highly reactive as compared to 2-bromopyridine. From the UV-vis and ICP-AES measurements, a significant amount of leached Pd(ii) was observed in the coupling with 2-bromopyridine as compared with 2-chloropyridine, indicating that the leaching process might be a crucial factor in diminishing the reactivity.
Dhital, Raghu Nath,Kamonsatikul, Choavarit,Somsook, Ekasith,Sakurai, Hidehiro
p. 3030 - 3035
(2013/11/06)

Organocatalytic functionalization of heteroaromatic N-oxides with C-nucleophiles using in situ generated onium amide bases
Organocatalytic functionalization of heteroaromatic N-oxides was investigated using in situ generated onium amide bases, and C-nucleophiles were efficiently introduced by the sequential addition-elimination reaction under metal-free conditions, affording 2-substituted nitrogen heteroaromatics generally in good to high yields. The Royal Society of Chemistry 2013.
Inamoto, Kiyofumi,Araki, Yuta,Kikkawa, Shoko,Yonemoto, Misato,Tanaka, Yoshiyuki,Kondo, Yoshinori
p. 4438 - 4441
(2013/08/23)

Acceptorless dehydrogenation of nitrogen heterocycles with a versatile iridium catalyst
Gas up: A cyclometalated iridium complex is found to catalyze the dehydrogenation of various benzofused N-heterocycles, thus releasing H 2. Driven by as low as 0.1 mol % catalyst, the reaction affords quinolines, indoles, quinoxalines, isoquinolines, and β-carbolines in high yields. Copyright
Wu, Jianjun,Talwar, Dinesh,Johnston, Steven,Yan, Ming,Xiao, Jianliang
supporting information
p. 6983 - 6987
(2013/07/26)

An efficient one pot transfer hydrogenation and N-alkylation of quinolines with alcohols mediated by Pd/C/Zn
A Pd/C/Zn mixture with alcohols has been revealed to be an efficient transfer hydrogenation system to quinolines. Furthermore, the metals mixture is able to activate alcohols as N-alkylating agents in a hydrogen autotransfer process. 1,2,3,4-Tetrahydroquinolines and N-alkylated tetrahydroquinolines from quinolines have been obtained with excellent yields in one step.
Abarca, Belen,Adam, Rosa,Ballesteros, Rafael
experimental part
p. 1826 - 1833
(2012/04/23)

TRANSITION METAL COMPLEX AND PROCESS FOR PRODUCING CONJUGATED AROMATIC COMPOUND WITH THE TRANSITION METAL COMPLEX
A transition metal complex obtained by contacting a bipyridine compound represented by the formula (1): wherein R1, R2 and R3 represent a C1-C10 alkyl group which may be substituted, etc., and R4 and R5 represent a hydrogen atom etc., with a compound of a transition metal belonging to Group 9, 10 or 11, and a process for producing a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups are bonded to an aromatic ring with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) being structurally different from the above-mentioned aromatic compound (A) and having one or two leaving groups bonded to an aromatic ring, in the presence of said transition metal complex.
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(2010/06/17)

METHOD FOR PRODUCING CONJUGATED AROMATIC COMPOUND
A method for producing a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups are bonded to an aromatic ring with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) being structurally different from the above-mentioned aromatic compound (A) and having one or two leaving groups bonded to an aromatic ring, in the presence of a nickel compound, a ligand, a manganese salt and a metal reducing agent.
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(2010/10/05)

Heteroaryl cross-coupling as an entry toward the synthesis of lavendamycin analogues: A model study
(Chemical Equation Presented) ABC analogues of the antitumor antibiotic lavendamycin, which contain the key metal chelation site and redox-active quinone unit essential for biological activity, were prepared via the palladium(0)-catalyzed cross-coupling reaction of various 2-haloheteroaromatics with 2-stannylated pyridines and quinolines. Using the Stille reaction, 2-bromo substituted quinolines and 1-bromoisoquinolines were found to undergo efficient coupling with 2-pyridinylstannanes to provide unsymmetrical heterobiaryl derivatives. While the Stille reaction using the reverse coupling partners (i.e., 2-quinolinylstannanes and haloheteroaromatics) had not received much attention in the literature, we found that this alternative coupling reaction efficiently provided several new heterobiaryl derivatives. The gold-catalyzed intramolecular cycloisomerization of N-(prop-2-ynyl)-1H-indole-2-carboxamide smoothly afforded a β-carbolinone derivative that was subsequently used for a Pd(0)-catalyzed cross-coupling directed toward the synthesis of lavendamycin analogues.
Verniest, Guido,Wang, Xingpo,De Kimpe, Norbert,Padwa, Albert
supporting information; experimental part
p. 424 - 433
(2010/03/30)

Synthesis of n-chloroquinolines and n-ethynylquinolines (n=2, 4, 8): Homo and heterocoupling reactions
The n-(ethynyl)quinolines were satisfactorily prepared by heterocoupling reaction between the appropriate n-chloroquinoline and 2-methyl-3-butyn-2-ol, catalyzed by palladium, followed by treatment with a catalytic amount of powdered sodium hydroxide in toluene. The n-(ethynyl)quinolines were transformed in the corresponding conjugate 1,4-bis[n′-(quinolyl)]buta-1,3-diynes by oxidative dimerization, catalyzed by cuprous chloride, with excellent yields. Moreover, the heterocoupling between n′-haloquinoline and n′-(ethynyl)quinoline (n′, 2′ or 3′), catalyzed by palladium, gives 2′,2′-bis(quinoline) or 1,2-di(3′-quinolyl) ethyne, respectively. The same coupling reaction with zerovalent nickel complexes, gives a mixture of 1,2,4- and 1,3,5-tri(n′-quinolyl)benzene.
Rodríguez, J. Gonzalo,De Los Rios, Cristobal,Lafuente, Antonio
p. 9042 - 9051
(2007/10/03)

Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids
Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides and chlorides undergoes Suzuki cross-coupling with alkylboronic acids in good yields. Several alkyl substituents such as ethyl, n-butyl, n-octyl, isobutyl or 2,2-dimethylpropyl on the alkylboronic acids have been successfully used. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides.
Kondolff, Isabelle,Doucet, Henri,Santelli, Maurice
p. 3813 - 3818
(2007/10/03)

Synthesis and reactivity of lithium tri(quinolinyl)magnesates
2-, 3- and 4-Bromoquinolines were converted to the corresponding lithium tri(quinolinyl)magnesates at -10°C when exposed to Bu3MgLi in THF. The resulting organomagnesium derivatives were quenched with various electrophiles or involved in metal-catalyzed coupling reactions with heteroaryl halides to afford functionalized quinolines.
Dumouchel, Sylvain,Mongin, Florence,Trécourt, Fran?ois,Quéguiner, Guy
p. 8629 - 8640
(2007/10/03)

Method for the catalytic production of substituted bipyridyl derivatives
The invention relates to a process for the preparation of bipyridyls by converting at least one pyridine of the formula (III) in which S′, S″, S′″, S″″ and S′″″, independently of one another, are identical or different and are hydrogen, (C1-C18)-alkyl, alkoxy-(C1-C18), acyloxy-(C1-C18), aryloxy-(C1-C18), perfluoroacyloxy-(C1-C8), NO2, (C1-C18)-aryl, (C1-C18)-heteroaryl, halogen, hydroxyl, nitro, nitroso, CN, COOH, CHO, PO3H2, SO3H, SO2R, SOR, NH2, NH-alkyl-(C1-C18), N-alkyl2-(C1-C18), protected amine, CF3, NHCO-alkyl-(C1-C4), N-alkyl-(C1-C4)-CO-alkyl-(C1-C4), COO-alkyl-(C1-C18), CONH2, CO-alkyl-(C1-C18), NHCOH, NHCOO-alkyl-(C1-C4), CO-(C1-C18)-aryl, COO-(C1-C18)-aryl, CHCH-CO2-alkyl-(C1-C18), CHCHCO2H, PO-phenyl2, PO-alkyl2-(C1-C4), (COO?)n(cation)n+, (PO32?)n(cation)2n+, (SO3?)n(cation)n+and/or (O?)n(cation)n+, where optionally S′, S″, S′″, S″″ and/or S′″″ among one another together form one or more aliphatic and/or aromatic rings and/or in which optionally S′, S″, S′″, S″″and/or S′″″forms a bridge to at least one further pyridine of the formula (III) and/or in which optionally the radicals S′, S″, S′″, S″″, and/or S′″″ have the meanings given above and are substituted by at least one radical which has the meaning given above for S′, S″, S′″, S″″ and/or S′″″ in water in the presence of an alcohol, a base, a palladium catalyst and optionally one or more further solvents at a temperature of 0-200° C.
-
(2008/06/13)

A photochromic system based on photochemical or thermal chelate exchange on Ru(phen)2L2+ (L = diimine or dinitrile ligand)
In the presence of a bidentate chelate containing two convergent nitrile groups, Ru(phen)2L2+ (L = sterically hindering aromatic diimine ligand; phen = 1,10-phenanthroline) undergoes a photochemical reaction leading to quantitative replacement of the diimine by the bis-nitrile ligand; the reverse reaction takes place upon heating, also quantitatively.
Baranoff,Collin,Furusho,Laemmel,Sauvage
p. 1935 - 1936
(2007/10/03)

Catalytic alternative of the Ullman reaction
Symmetrical functionalized biaryls and biheterocycles could be obtained in good yield via homocoupling of aryl halides by using Pd(OAc)2 as catalyst with base and isopropanol. This alternative of the Ullmann reaction has proved to be compatible with sensitive functional groups.
Hassan, Jwanro,Penalva, Vincent,Lavenot, Laurence,Gozzi, Christel,Lemaire, Marc
p. 13793 - 13804
(2007/10/03)

Anion-radical 1,4-transition of oxygen in the quinoline-N-oxides
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Kurbatova,Kurbatov
p. 905 - 905
(2007/10/03)

A New Reaction of Reductive Dehydrodimerization of Quinoline N-Oxide
-
Kurbatova,Kurbatov,Khushvakhtova
p. 578 - 579
(2007/10/03)

A Convenient Synthetic Route to bis-Heteroaromatic and bis-Heterocyclic Compounds Promoted by Liganded Nickel Complex Reducing Agents.
A number of nitrogen, sulfur or oxygen containing bis-heteroaromatic or bis-heterocyclic derivatives have been synthesized in good to excellent yields by homocoupling of the corresponding halogenated compounds in the presence of liganded (triphenylphosphine or 2,2'-bipyridine) nickel Complex Reducing Agents in THF or DME at 63 deg C.
Forst, Yves,Becker, Sandrine,Caubere, Paul
p. 11893 - 11902
(2007/10/02)

SRN1 reactions of aryl halides with carbanions initiated by sodium amalgam in liquid ammonia
The reaction of 1-chloronaphthalene with acetone (2a) and acetophenone (2b) enolate ions was initiated by sodium amalgam [Na(Hg)] in liquid ammonia giving good yields of the substitution products 3a and 3b respectively. 2-Chloroquinoline and 2-chloropyridine gave good yields of substitution product with 2b, and moderate to good yields with 2a. 4-Bromobenzophenone and 2a gave 78% of the substitution product 5. With aryl halides whose radical anions fragment fast and consequently close to the Na(Hg) surface, such as bromobenzene and p-bromoanisole, only dehalogenation products were observed. However, when benzonitrile was used as a redox catalyst, about 50% of the substitution product 6 was obtained with p-bromoanisole and 2a. However, with the more reactive carbanionic nucleophile, such as anthrone anion 4, good yields of the substitution product 7 were obtained with bromobenzene. In all these reactions neither reduction of the aromatic moiety nor the ketone functionality was observed. It is therefore suggested that Na(Hg) amalgam initiates these SRN1 reactions.
Austin, Eduardo,Ferrayoli, Carlos G.,Alonso, Ruben A.,Rossi, Roberto A.
p. 4495 - 4502
(2007/10/02)

Reductive electrochemical carboxylation in context with quantum chemical calculations
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Hess,Komenda,Pospichal
p. 900 - 904
(2007/10/02)

A cross-coupling reaction of methylsulfinylarene
-
Wakabhayashi,Tanaka,Kubo,Uenishi,Oae
p. 3848 - 3850
(2007/10/02)

FORMATION OF PHENYL SUBSTITUTED HETEROAROMATICS BY LIGAND COUPLING IN THE REACTION BETWEEN HETEROARYL SULFOXIDES WITH PHENYL GRIGNARD REAGENT
In the reaction of heteroaryl alkyl sulfoxides with phenylmagnesium bromide, phenyl group was found to couple predominantly with 2-quinolyl group and 2-pyrimidinyl group.
Oae, Shigeru,Takeda, Takashi,Wakabayashi, Shoji
p. 99 - 102
(2007/10/02)

NEW REACTIONS OF PYRIDINES AND TOTAL SYNTHESIS OF THE FUNGAL TOXIN ORELLANINE
Dihalogenated pyridines react easily with sulphur nucleophiles, in dipolar aprotic solvents (DMF), to afford the products of mono- or of bis-substitution depending on the experimental conditions.On the contrary, with oxygen nucleophiles the bis-substituted products can be obtained only with some particular substrates.A new and efficient procedure to effect the homo-coupling of halogenoarenes will be presented.This reaction, wich occurs under the influence of low-valent nickel complexes, allowed us to effect the total synthesis of Orellanine, the lethal toxin of Cortinarius orellanus mushroom, as well as the syntheses of its decompositionproducts Orellinine and Orelline.The chemical properties of these three products and their behaviour towards UV irradiation will be presented and discussed.
Tiecco, Marcello
p. 1009 - 1020
(2007/10/02)

THE COUPLING OF ORGANIC GROUPS BY THE ELECTROCHEMICAL REDUCTION OF ORGANIC HALIDES: CATALYSIS BY 2,2'-BIPYRIDINENICKEL COMPLEXES
The electrochemical reduction of a dilute solution of NiX2bipy (bipy = 2,2'-bipyridine) in N-methylpyrrolidone gives the corresponding Ni0 complex, which undergoes oxidative addition with an excess of an organic halide RX to form RNiX.Decomposition of RNiX gives the dimer R2 in good yield and nickel(II).The nickel(0) species is regenerated to give an electrocatalytic process.The possible mechanism of these reactions is discussed briefly.
Rollin, Yolande,Troupel, Michel,Tuck, Dennis G.,Perichon, Jacques
p. 131 - 138
(2007/10/02)

ACTIVATION OF REDUCING AGENTS. SODIUM HYDRIDE CONTAINING COMPLEX REDUCING AGENTS 23. SYMMETRICAL COUPLING OF NITROGEN-CONTAINING HETEROCYCLIC HALIDES
The preparation of NiCRA (NaH-tBuONa-Ni(OAc)2) in the presence of PPh3 leads to a reagent (termed NiCRA-PPh3) which is shown to be one of the most efficient Ni containing reagents reported so far for the homocoupling of heteroaromatic halides.
Vanderesse, R.,Lourak, M.,Fort, Y.,Caubere, P.
p. 5483 - 5486
(2007/10/02)

Chemical Properties

Appearance/Colour :slightly yellow to light beige shiny flakes
Melting Point: 192-195 °C(lit.)
Boiling Point: 456.1 °C at 760 mmHg
Flash Point:203.6 °C
Density: 1.223 g/cm³
Solubility:1.02mg/l
Storage Temp.:Store at +15°C to +25°C.
Refractive Index: 1.6300 (estimate)
PKA: 2.19±0.61(Predicted)
BRN: 187259
PSA: 25.78000
LogP: 4.45000

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Article Database

119-91-5

Articles about 119-91-5Total 53 be found

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Chemical Properties

Appearance/Colour :slightly yellow to light beige shiny flakes

Melting Point: 192-195 °C(lit.)

Boiling Point: 456.1 °C at 760 mmHg

Flash Point:203.6 °C

Density: 1.223 g/cm³

Solubility:1.02mg/l

Storage Temp.:Store at +15°C to +25°C.

Refractive Index: 1.6300 (estimate)

PKA: 2.19±0.61(Predicted)

BRN: 187259

PSA: 25.78000

LogP: 4.45000

Global suppliers and manufacturers of 119-91-5total 114 suppliers on LookChem

Article Database

119-91-5

Articles about 119-91-5Total 53 be found

More Articles about upstream products of 119-91-5

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Chemical Properties

Appearance/Colour :slightly yellow to light beige shiny flakes

Melting Point: 192-195 °C(lit.)

Boiling Point: 456.1 °C at 760 mmHg

Flash Point:203.6 °C

Density: 1.223 g/cm3

Solubility:1.02mg/l

Storage Temp.:Store at +15°C to +25°C.

Refractive Index: 1.6300 (estimate)

PKA: 2.19±0.61(Predicted)

BRN: 187259

PSA: 25.78000

LogP: 4.45000

Global suppliers and manufacturers of 119-91-5total 114 suppliers on LookChem

Density: 1.223 g/cm³