- 3,3'-((Arylmethylene)bis(4-methoxy-3,1-phenylene)) dipyridine derivatives as convenient ligands for Suzuki–Miyaura chemo- and homoselective cross-coupling reactions
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Four novel N,N-bidentate triarylmethane-based ligands bearing β-pyridyl residues have been prepared and the catalytic activity of their in-situ generated palladium complexes were studied in the Suzuki–Miyaura cross-coupling reactions. Air and moisture stable 3,3'-((arylmethylene)bis(4-methoxy-3,1-phenylene))dipyridines L1-3 showed excellent activity in the Suzuki coupling reactions of aryl halides with aryl boronic acids under thermal and sonochemical reaction conditions. The described methodology provided good to high yields in short reaction times at ambient conditions. Moreover, it offered a straightforward way for Suzuki–Miyaura chemo- and homoselective cross-coupling of aryl halides with phenyl boronic acid. The structures of synthesized compounds were fully characterized by FT-IR, 1H-NMR, 13C-NMR, and elemental analyses. The coordination of palladium acetate to nitrogen sites of L1 was also studied using FTIR spectroscopy, EDX analysis and SEM observations. Graphic abstract: The in-situ generated Pd-complexes of N,N-bidentate ligands L1-3 are described as robust and highly effective catalytic systems for the Suzuki cross-coupling of aryl halides with aryl boronic acids under thermal and sonochemical reaction conditions.[Figure not available: see fulltext.]
- Hosseini, Raziyeh,Mohammadiannejad, Kazem,Ranjbar-Karimi, Reza
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- ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
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A compound useful as a host material in phosphorescent light emitting devices is disclosed. The compound has the following formula: in which R represents an adjacent di-substitution having the following formula fused to ring A:
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Paragraph 130; 0131
(2019/03/15)
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- C6-Selective Direct Arylation of 2-Phenylpyridine via an Activated N-methylpyridinium Salt: A Combined Experimental and Theoretical Study
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An elegant pre-activation strategy, based on the formation of N-methylpyridinium iodide salts for C6-selective direct arylation of 2-phenylpyridines using Pd/Cu cooperative catalysis, has been developed. By this methodology, a wide range of unsymmetrical 2, 6-diarylpyridines were synthesized with high reactivity and regioselectivity as well as good functional group tolerance. In particular, challenging substrates bearing electron donating groups (EDGs), such as OMe, NMe2, were also successfully employed in this reaction. Deuterium incorporation studies revealed that the C?H bond acidity is improved significantly in N-methylpyridinium salts compared with their N-Oxide and N-iminopyridinium ylide counterparts, thus solving the long-standing problem associated with previous strategies for the synthesis of diaryl pyridines. Finally, the control experiments and DFT calculations supported a Pd-catalyzed and Cu-mediated mechanism in which a carbenoid copper species that is formed in-situ from N-methylpyridinium salts, participates in a Pd-catalyzed arylation followed by an iodide-promoted N-demethylation process. (Figure presented.).
- Yin, Changzhen,Zhong, Kangbao,Li, Wenjing,Yang, Xiao,Sun, Rui,Zhang, Chunchun,Zheng, Xueli,Yuan, Maolin,Li, Ruixiang,Lan, Yu,Fu, Haiyan,Chen, Hua
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supporting information
p. 3990 - 3998
(2018/09/12)
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- Metal-free deoxygenation and reductive disilylation of nitroarenes by organosilicon reducing reagents
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A metal-free deoxygenation and reductive disilylation of nitroarenes was achieved using N,N’-bis(trime-thylsilyl)-4,4’-bipyridinylidene (1) under mild and neutral reaction conditions, and a broad functional group tolerance was possible in this reaction. Mono-deoxygenation, giving a synthetically valuable N,O-bis(trimethylsilyl)phe-nylhydroxylamine (7a) as a readily available and safe phenylnitrene source from nitrobenzene, and double-deoxy-genation, giving N,N-bis(trimethylsilyl)anilines 8, were easily controlled by varying the amounts of 1 and reaction temperature as well as adding dibenzothiophene (DBTP). Reaction of 2-arylnitrobenzenes with 1 resulted in the formation of the corresponding carbazoles 14 via in situ-gen-erated phenylnitrene species derived by thermolysis of N,O-bis(trimethylsilyl)phenylhydroxylamines 7, followed by their subsequent intramolecular C H insertion. In addition, the intramolecular N N coupling reaction proceeded in the reduction of 2,2’-dinitrobiphenyl derivatives by 1, giving the corresponding benzo[c]cinnolines.
- Bhattacharjee, Argha,Hosoya, Hiromu,Ikeda, Hideaki,Nishi, Kohei,Tsurugi, Hayato,Mashima, Kazushi
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supporting information
p. 11278 - 11282
(2018/10/20)
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- Disubstituted derivative of carboline, and preparation method and application thereof
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The invention especially relates to a disubstituted derivative of carboline, and a preparation method and application thereof, belonging to the technical field of organic electroluminescent materials. The disubstituted derivative of carboline can be used
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Paragraph 0067; 0068; 0069
(2017/08/30)
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- Manipulation of electron deficiency of δ-carboline derivatives as bipolar hosts for blue phosphorescent organic light-emitting diodes with high efficiency at 1000 cd m-2
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The effect of different linkages on thermal, electrochemical, photophysical, and optoelectronic properties was discussed in detail to illuminate the structure-property relationship of four δ-carboline derivatives, 5-(3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-
- Zhang, Zhen,Xie, Jingwei,Wang, Zixing,Shen, Bowen,Wang, Hedan,Li, Minjie,Zhang, Jianhua,Cao, Jin
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p. 4226 - 4235
(2016/06/01)
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- NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
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The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device adopting the same, and more specifically, to an organic electroluminescent compound represented by chemical formula 1 below. In the chemical formula 1, ring A and ring B are independently a monocyclic or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, a five- or six-membered heteroaromatic ring fused with an aromatic ring, or a monocyclic or polycyclic aromatic ring fused with a five- or six-membered heteroaromatic ring, where the ring A and ring B cannot both be a monocyclic aromatic ring. The organic electroluminescent compound according to the present invention shows good luminous efficiency, and superior material color purity and lifetime characteristics, thereby enabling manufacture of an OLED device with excellent driving time.COPYRIGHT KIPO 2016
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Paragraph 0113-0115
(2016/10/10)
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- TRKA KINASE INHIBITORS, COMPOSITIONS AND METHODS THEREOF
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The present invention is directed to six membered heteroaryl benzamide compounds of formula (I), which are tropomyosin-related kinase (Trk) family protein kinase inhibitors, and hence are useful in the treatment of pain, inflammation, cancer, restenosis, atherosclerosis, psoriasis, thrombosis, a disease, disorder, injury, or malfunction relating to dysmyelination or demyelination or a disease or disorder associated with abnormal activities of nerve growth factor (NGF) receptor TrkA.
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Page/Page column 57; 58
(2015/12/30)
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- Complete Switch of Selectivity in the C-H Alkenylation and Hydroarylation Catalyzed by Iridium: The Role of Directing Groups
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A complete switch in the CpIr(III)-catalyzed paths between C-H olefination and hydroarylation was found to be crucially dependent on the type of directing groups. This dichotomy in product distribution was correlated to the efficiency in attaining syn-coplanarity of olefin-inserted 7-membered iridacycles. Theoretical studies support our hypothesis that the degree of flexibility of this key intermediate modulates the β-H elimination, which ultimately affords the observed chemoselectivity.
- Kim, Jiyu,Park, Sung-Woo,Baik, Mu-Hyun,Chang, Sukbok
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supporting information
p. 13448 - 13451
(2015/11/09)
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- N-methyliminodiacetic acid as a simple and highly efficient ligand for palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl chlorides
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A simple, air-stable, inexpensive and easily prepared molecule, N-methyliminodiacetic acid (MIDA), is reported as a ligand for palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of phenylboronic acid with aryl chlorides. The yield of the corresponding Suzuki coupling reaction is up to around 90% at both high temperature of 80°C and room temperature under ambient atmosphere.
- Qi, Liang,Zhou, Xiuling,Li, Xiaogang,Li, Wei,Lv, Meiyun,Guo, Mengping
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p. 244 - 246
(2015/03/30)
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- Synthesis and characterization of hydrophilic theophylline base compounds and their use as ligands in the microwave assisted Suzuki-Miyaura couplings of halopyridines in water Dedicated to the memory of Prof. Dr. Armando Cabrera Ortiz pioneer of Catalysis in Mexico. Great Researcher but above all a Great Human Being
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Xanthine derivatives, caffeine (L1), theobromine (L2), theophylline (L3), 7-(β-hydroxyethyltheophylline) (L4), (7-(2,3-dihydroxypropyl)theophylline) (L5), and theophylline 7-acetic acid (L6) and the acetylated derivatives of the later three (L7-L9) were employed as ligands for the in situ palladium catalyzed Suzuki-Miyaura cross couplings of a series of halogenated pyridines. Optimized conditions were found where the diacetylated ligand (L8) was determined to be the best for this process, producing good to excellent yields in the couplings of halogenated anilines with phenylboronic acid under mild reaction conditions in water using microwave irradiation.
- Conelly-Espinosa, Patricia,Toscano, Ruben A.,Morales-Morales, David
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p. 5841 - 5845
(2015/01/09)
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- First synthesis of benzopyridoiodolium salts and twofold Buchwald-Hartwig amination for the total synthesis of quindoline
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The first synthesis of cyclic benzopyridoiodolium salts is described. These hypervalent iodine intermediates are used in an efficient strategy for the construction of the -carboline core. This novel approach involves a twofold palladium-catalyzed Buchwald
- Letessier, Julien,Detert, Heiner
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scheme or table
p. 290 - 296
(2012/04/17)
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- C-H arylation of pyridines: High regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring
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We report a new catalytic protocol for highly selective C-H arylation of pyridines containing common and synthetically versatile electron-withdrawing substituents (NO2, CN, F and Cl). The new protocol expands the scope of catalytic azine functi
- Guo, Pengfei,Joo, Jung Min,Rakshit, Souvik,Sames, Dalibor
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supporting information; experimental part
p. 16338 - 16341
(2011/11/29)
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- Facile one-pot direct arylation and alkylation of nitropyridine N -oxides with grignard reagents
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Facile arylation and alkylation of nitropyridine N-oxides were developed through the reactions of Grignard reagents with nitropyridine N-oxides. For the same 4-nitropyridine N-oxide, arylation occurred at the 2- (or 6-) position, whereas alkylation occurred at the 3-position in an adjustably site-selective manner. The cooperative action of the two groups was discovered in the reactions of 3-nitropyridine N-oxides. This protocol can find wide applications in building various pyridine compounds as illustrated in total syntheses of Emoxipin and Caerulomycin A and E.
- Zhang, Fang,Duan, Xin-Fang
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supporting information; experimental part
p. 6102 - 6105
(2012/01/06)
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- NOVEL MICROBIOCIDES
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Compounds of the formula (I) in which the substituents are as defined in claim 1 are suitable for use as microbiocides.
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Page/Page column 85-86
(2008/12/08)
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- RADIOLABELED NEUROKININ-1 RECEPTOR ANTAGONISTS
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The present invention is directed to radiolabeled neurokinin-1 receptor antagonists which are useful for the labeling and diagnostic imaging of neurokinin-1 receptors in mammals.
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- Palladium Charcoal-Catalyzed Suzuki-Miyaura Coupling to Obtain Arylpyridines and Arylquinolines
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A phosphine ligand, such as PPh3 or 2-(dicyclohexylphosphino)biphenyl, is essential for the Pd/C-catalyzed Suzuki-Miyaura coupling of halopyridines and haloquinolines, although it has been reported that the reaction of phenyl chlorides can be catalyzed by nonprereduced Pd/C without any additives. In the reactions of bromopyridines, bromoquinolines, 2-chloropyridines, and 2-chloroquinolines, PPh3 was effective enough to provide coupling products in good yields. However, in the reactions of 3-chloropyridine, 4-chloropyridine, and 6-chloroquinoline, sterically hindered 2-(dicyclohexylphosphino)biphenyl was indispensable as a ligand.
- Tagata, Tsuyoshi,Nishida, Mayumi
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p. 9412 - 9415
(2007/10/03)
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- 5-PHENYLBENZYLAMINE COMPOUNDS, PROCESS FOR THEIR PRODUCTION AND INTERMEDIATES FOR THEIR SYNTHESIS
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The present invention relates to a 5-phenylbenzylamine compound represented by the formula [1]: wherein Ring A represents a phenyl group having a substituent(s), ???Ra, Rb1 and Rb2 each represent hydrogen atom, a halogen a
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- F-18 radiolabeled neurokinin-1 receptor antagonists
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The present invention is directed to radiolabeled neurokinin-1 receptor antagonists which are useful for the labeling and diagnostic imaging of neurokinin-1 receptors in mammals.
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- Tetrazole NK1 receptor antagonists: The identification of an exceptionally potent orally active antiemetic compound
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The medicinal chemistry strategy which led to the identification of GR205171, an orally active non-peptide neurokinin-1 receptor antagonist that is the most potent broad-spectrum antiemetic agent reported to date.
- Armour,Chung,Congreve,Evans,Guntrip,Hubbard,Kay,Middlemiss,Mordaunt,Pegg,Vinader,Ward,Watson
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p. 1015 - 1020
(2007/10/03)
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- Palladium-catalysed cross-coupling reactions of arylboronic acids with π-deficient heteroaryl chlorides
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The palladium-catalysed cross-coupling reactions of arylboronic acids with a variety of π-deficient heteroaryl chlorides proceed in high yield. [1,4-Bis(diphenylphosphino)butane]palladium(II) dichloride was found to be a very satisfactory catalyst for monocyclic heteroaryl chlorides, whereas tetrakis(triphenylphosphine)palladium(O) was found to be excellent for a range of chloroquinoline derivatives.
- Ali,McKillop,Mitchell,Rebelo,Wallbank
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p. 8117 - 8126
(2007/10/02)
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- COUPLING OF HETEROARYL CHLORIDES WITH ARYLBORONIC ACIDS IN THE PRESENCE OF PALLADIUM(II) DICHLORIDE
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The cross-coupling of arylboronic acids with a variety of ?-deficient heteroaryl chlorides has been shown to occur in high yield in the presence of palladium(II) dichloride as catalyst.
- Mitchell, M. B.,Wallbank, P. J.
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p. 2273 - 2276
(2007/10/02)
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