- HETEROCYCLIC COMPOUNDS FOR MODULATING NR2F6
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The present disclosure relates to compounds capable of modulating the activity of NR2F6. The compounds of the disclosure may be used in methods for the prevention and/or the treatment of diseases and disorders associated with modulating NR2F6 activity.
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Paragraph 00524-00526
(2021/09/04)
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- Copper anchored on phosphorus g-C3N4as a highly efficient photocatalyst for the synthesis ofN-arylpyridin-2-amines
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A heterogeneous photocatalyst based on copper modified phosphorus doped g-C3N4(Cu/P-CN) has been prepared and characterized. This recyclable catalyst exhibited high photocatalytic activity for the synthesis ofN-arylpyridin-2-amine derivatives by the reaction of 2-aminopyridine and aryl boronic acid at room temperature under the irradiation of blue light. Importantly, the range of substrates for this coupling reaction has been expanded to include aryl boronic acids with strong electron-withdrawing groups as viable raw materials. In addition, this heterogeneous catalyst can be used at least 6 times while maintaining its catalytic activity.
- Di, Jia-Qi,Zhang, Mo,Chen, Yu-Xuan,Wang, Jin-Xin,Geng, Shan-Shan,Tang, Jia-Qi,Zhang, Zhan-Hui
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p. 1041 - 1049
(2021/02/09)
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- Growing the molecular architecture of imidazole-like ligands in HO-1 complexes
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Up-regulation of HO-1 had been frequently reported in different cases and types of human malignancies. Since poor clinical outcomes are reported in these cases, this enzyme's inhibition is considered a valuable and proven anticancer approach. To identify
- Floresta, Giuseppe,Fallica, Antonino N.,Salerno, Loredana,Sorrenti, Valeria,Pittalà, Valeria,Rescifina, Antonio
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- Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni(ii) β-oxodithioester-dppe]+; Their use as a catalyst for Chan-Lam coupling
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Novel heteroleptic [Ni(ii) β-oxodithioester-dppe]+PF6- complexes (β-oxodithioester = methyl-3-hydroxy-3-benzyl-2-propenedithioate L1 1, methyl-3-hydroxy-3-(p-methoxyphenyl)-2-propenedithioate L2 2, methyl-3-hydroxy-3-(naphthyl)-2-propenedithioate L3 3, methyl-3-hydroxy-3-(p-chlorophenyl)-2-propenedithioate L4 4, methyl-3-hydroxy-3-(p-bromophenyl)-2-propenedithioate L5 5 and methyl-3-hydroxy-3-(p-cyanophenyl)-2-propenedithioate L6 6) have been synthesized and characterized by elemental (C, H, N) analysis, ESI-MS, IR, UV-visible, 1H, 13C{1H}, 31P{1H} and 19F{1H} NMR spectroscopy. The distorted square planar structures of the isomorphous cationic complexes 2, 3, 4 and 5 have been determined by X-ray crystallography. The catalytic activities of 1-6 were investigated for the Chan-Lam coupling reaction involving arylboronic acids and amines to afford N-arylated products in good to excellent yields under mild conditions with 1 mol% catalyst loading. This catalytic protocol offers significant functional group tolerance, and is endowed with a broad substrate scope. This journal is
- Kumari, Kavita,Kumar, Saurabh,Singh, Krishna Nand,Drew, Michael G. B.,Singh, Nanhai
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p. 12143 - 12153
(2020/07/30)
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- Chan-Evans-Lam C?N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle
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In the present study, we report the synthesis of a series of copper(II) complexes with a wide range of ligands and their testing in the copper catalyzed Chan-Evans-Lam (CEL) coupling of aniline and phenylboronic acid. The efficiency of the coupling was directly connected with the ease of the reduction of Cu(II) to Cu(I) of the complexes. The most efficient catalyst was derived from 4-t-butyl-2,5-bis[(quinolinylimino)methyl]phenolate and two Cu(II) ions. Depending on the counter-anion nature and the concentration of the reaction mixture, the reaction can be directed to predominant C?N-bond formation. Forty-three derivatives of diphenylamine were prepared under the optimized conditions. The proposed mechanism of the catalysis was based on the reduction potential of a series of complexes, molecular weight measurements of the catalytic complex in MeOH and the kinetic studies of aniline and phenylboronic acid coupling. In addition, an 1H NMR experiment in a sealed NMR tube, without external oxygen supply available, proved that no complete Cu(II) to Cu(I) conversion was observed under the condition, ruling out the usually accepted mechanism of the C?N coupling, which included the oxygenation of the intermediately formed Cu(I) complexes after the key step of C?N conversion had already been completed. Instead, a mechanism was proposed, involving an oxygen molecule coordinated to two copper ions in the key C?N bond formation without any detectable conversion of the Cu(II) complexes to Cu(I).
- Akatyev, Nikolay,Il'in, Mikhail,Il'in, Mikhail,Peregudova, Svetlana,Peregudov, Alexander,Buyanovskaya, Anastasiya,Kudryavtsev, Kirill,Dubovik, Alexander,Grinberg, Valerij,Orlov, Victor,Pavlov, Alexander,Novikov, Valentin,Volkov, Ilya,Belokon, Yuri
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p. 3010 - 3021
(2020/04/29)
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- Preparation and characterization of isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles as a novel magnetic catalyst for the Ullmann coupling reaction
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Isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles (Cu-IS-AMBA-MNPs) as a new catalyst was designed, prepared and characterized by appropriate analyses. The heterogeneous reusable catalyst was successfully used for the efficient and widespread syntheses of diaryl ethers and diarylamines via the Ullmann coupling reaction. This green catalyst was easily removed, reused several times with no significant loss of its activity, and provided a clean synthesis with excellent yield and reduced time.
- Khodaei, Mohammad Mehdi,Alizadeh, Abdolhamid,Haghipour, Maryam
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p. 2727 - 2747
(2019/02/13)
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- Nano CoCuFe2O4-catalyzed coupling reaction of arylboronic acid with amines and thiols: An atom-economic and ligand-free route to access unsymmetrical amines and sulfides
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An efficient protocol was developed for the nano CoCuFe2O4-catalyzed C-N and C-S bond formation. By this catalytic system, both amine and sulfide-based structural motifs were formed efficiently in aryl halide-free route. The amination reaction of phenyl boronic acid with various types of amines was conducted under ligand-free conditions, in ethanol as a green solvent at 60°C. Unsymmetrical diaryl/aryl alkyl sulfide synthesis via the coupling reaction of arylboronic acids with thiols was also conducted. The nano cobalt-copper ferrite was used as a heterogenous efficient, inexpensive, magnetically separable and recyclable catalyst that can be used for several cycles.
- Moghaddam, Firouz Matloubi,Pourkaveh, Raheleh,Gholamtajari, Milad
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- Immobilization of nickel ions onto the magnetic nanocomposite based on cross-linked melamine groups: Effective heterogeneous catalyst for N-Arylation of Arylboronic acids
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A new magnetic heterogeneous catalyst was synthesized by immobilization of nickel ions onto a cross-linked polymeric nanocomposite composed of cyanuric chloride, ethylenediamine and functionalized magnetic nanoparticles. The resulting nitrogen rich support was capable of adsorbing large amounts of nickel ions (1.20 mmol g?1). The synthesized catalyst was characterized using AAS, TEM, FT-IR, EDX, TGA, SEM, BET and XRD techniques. The performance of the prepared catalyst was investigated in the C-N coupling of arylamines with aryl boronic acids. The reaction was carried out under a mild condition and good to moderate to good yields of products was obtained using only 5.0 mol% of the catalyst. The catalyst was easily recovered and reused for at least 7 times without any significant loss of its activity.
- Pourjavadi, Ali,Keshavarzi, Nahid,Moghaddam, Firouz Matloubi,Hosseini, Seyed Hassan
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- Iodine-catalyzed synthesis of N, N ′-diaryl-o-phenylenediamines from cyclohexanones and anilines using DMSO and O2 as oxidants
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A novel I2-catalyzed cross-dehydrogenative aromatization of cyclohexanones and anilines to synthesize N,N′-diaryl-o-phenylenediamines has been unprecedentedly developed with dimethyl sulfoxide and oxygen employed as mild terminal oxidants. To prove the rationality of the two separate dehydration steps of the proposed mechanism, a resulting I2-catalyzed cross-dehydrogenative aromatization of cyclohexenones and anilines to synthesize diarylamines has also been reported.
- Xiong, Mingteng,Gao, Zhan,Liang, Xiao,Cai, Pengfei,Zhu, Heping,Pan, Yuanjiang
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supporting information
p. 9679 - 9682
(2018/09/10)
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- Metal-free synthesis of secondary amines by the reaction of tosyl triazene and aryl boronic acid
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A metal free noncatalytic amination process has been developed for the synthesis of N-substituted aniline using a new amine source. The amine source p-toluene sulfonyl triazene (PhN?NNHTs) has been prepared by treating aryldiazonium salt with p-tosylamide. Various unsymmetrical amines could be synthesized by treating this reagent and boronic acid in toluene at 110 °C in the presence of DBU and 4 ? molecular sieve. A large variety of N-substituted aniline could be synthesized with moderate yield.
- Sarma, Manas Jyoti,Phukan, Prodeep
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p. 656 - 662
(2018/02/19)
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- Discovery of 2-((4,6-dimethylpyrimidin-2-yl)thio)-N-phenylacetamide derivatives as new potent and selective human sirtuin 2 inhibitors
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Human sirtuin 2 (SIRT2) plays pivotal roles in multiple biological processes such as cell cycle regulation, autophagy, immune and inflammatory responses. Dysregulation of SIRT2 was considered as a main aspect contributing to several human diseases, including cancer. Development of new potent and selective SIRT2 inhibitors is currently desirable, which may provide a new strategy for treatment of related diseases. Herein, a structure-based optimization approach led to new 2-((4,6-dimethylpyrimidin-2-yl)thio)-N-phenylacetamide derivatives as SIRT2 inhibitors. SAR analyses with new synthesized derivatives revealed a number of new potent SIRT2 inhibitors, among which 28e is the most potent inhibitor with an IC50 value of 42?nM. The selectivity analyses found that 28e has a very good selectivity to SIRT2 over SIRT1 and SIRT3. In cellular assays, 28e showed a potent ability to inhibit human breast cancer cell line MCF-7 and increase the acetylation of α-tubulin in a dose-dependent manner. This study will aid further efforts to develop highly potent and selective SIRT2 inhibitors for the treatment of cancer and other related diseases.
- Yang, Lingling,Ma, Xiaobo,Yuan, Chen,He, Yanying,Li, Ling,Fang, Sha,Xia, Wei,He, Tao,Qian, Shan,Xu, Zhihong,Li, Guobo,Wang, Zhouyu
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supporting information
p. 230 - 241
(2017/04/19)
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- Novel SIRT2 protein inhibitor and usage thereof in pharmacy
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The invention discloses a compound or salt, crystallographic form and solvate compounds of the compound acceptable in pharmacy, and the compound and the salt, crystallographic form, solvate compounds of the compound are shown as formula I, wherein X is selected from the formulas (please see the specifications for the formula); R1 is selected from aryl or ceteroary or substituted aryl or substituted ceteroary or from the formula (please see the specifications for the formula); R2 is selected from the formulas (please see the specifications for the formula); and R3 is selected from halogen or C1-C4 alkyl or C1-C4 alkoxy. The novel compound shown in formula I has the advantages that not only is good inhibitory activity achieved to SIRT2, but also the inhibiting effect is achieved to the tumor, and the novel compound has good pharmaceutical potentiality and provides a novel potential choice for the clinical medicament.
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Paragraph 0091; 0092
(2017/08/28)
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- A quick Chan-Lam C-N and C-S cross coupling at room temperature in the presence of square pyramidal [Cu(DMAP)4I]I as a catalyst
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A rapid and efficient protocol for C-N and C-S cross coupling has been developed using a new square pyramidal copper complex, [Cu(DMAP)4I]I. The complex was successfully synthesized via a disproportionation reaction of CuI and DMAP in DMSO. The catalytic activity of the complex was found to be excellent for Chan-Lam coupling reaction between aryl boronic acid and amine, amide, azide or thiol. The reaction could be carried out in the presence of only 2 mol% of the copper catalyst in methanol at room temperature within a short time.
- Roy, Subhasish,Sarma, Manas Jyoti,Kashyap, Bishwapran,Phukan, Prodeep
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supporting information
p. 1170 - 1173
(2016/01/15)
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- A method for preparing aromatic amine derivative
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The invention discloses a preparation method of a diarylamine ramification. The preparation method comprises the following steps: dissolving a phenylamine ramification, a phenylhydrazine ramification, a metal phthalocyanine ramification and a copper salt into a solvent, and reacting at -10 to 40 DEG C to obtain the diarylamine ramification. According to the preparation method, the phenylamine ramification and the phenylhydrazine ramification are taken as starting materials, so that raw materials are easy to obtain and plenty in variety; a product obtained by utilizing the method is plenty in type, can not only be directly used, but also be used for other further reactions; and no additive is required to be added. The preparation method disclosed by the invention has the advantages of short synthetic route, moderation in reaction condition, simple reaction operation and post-processing process, high yield and suitability for large-scale production.
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-
Paragraph 0096-0099
(2016/10/08)
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- CoPc/Cu(OAc)2-catalyzed N-arylation of amines with arylhydrazines leading to N-aryl amines
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The N-arylation of amines with arylhydrazines has been developed, achieving the selective cross-coupling of aryl radicals with amines to form N-aryl amines. The reaction uses air as an oxidant, CoPc and Cu(OAc)2as catalysts. The reaction proceeds under mild conditions in air through a relay process, arylhydrazines are oxidized to aryldiazenes by CoPc, further oxidized to aryl radicals by air (O2), which are trapped by Cu(OAc)2–amine complex, followed by reduction–elimination reaction to form N-aryl amines. Arylamines and arylhydrazines give the highest yields, but N-aryl-N-alkylamines and N-alkylamines can be used as well.
- Sun, Wang-Bin,Zhang, Pei-Zhi,Jiang, Tao,Li, Cheng-Kun,An, Li-Tao,Shoberu, Adedamola,Zou, Jian-Ping
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p. 6477 - 6483
(2016/09/23)
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- Synthesis and development of Chitosan anchored copper(II) Schiff base complexes as heterogeneous catalysts for N-arylation of amines
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Abstract The Chitosan anchored Cu(II) Schiff base complexes (C1-C3) have been synthesized and characterized by FTIR, UV, FE-SEM, EDAX, TGA, AAS and elemental analysis. These complexes have been found to be efficient and recyclable heterogeneous catalysts for the Chan-Lam C-N coupling reaction of various aromatic/aliphatic amines with arylboronic acid under mild reaction conditions. These complexes can be easily filtered out from the reaction medium and reused up to five times without significant loss of catalytic activity.
- Anuradha,Kumari, Shweta,Pathak, Devendra D.
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supporting information
p. 4135 - 4142
(2015/08/03)
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- Magnetically recyclable magnetite-palladium (Nanocat-Fe-Pd) nanocatalyst for the Buchwald-Hartwig reaction
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The immobilization of Pd on the magnetite surface afforded Nanocat-Fe-Pd using inexpensive precursors and its catalytic role in the Buchwald-Hartwig reaction for arylation of amines and amides was investigated; C-N bond formation was achieved in moderate to excellent yields and the catalyst could be separated and recycled up to five cycles by magnetic decantation without a significant loss in yield. This journal is the Partner Organisations 2014.
- Sa, Sofia,Gawande, Manoj B.,Velhinho, Alexandre,Veiga, Joao Pedro,Bundaleski, Nenad,Trigueiro, Joao,Tolstogouzov, Alexander,Teodoro, Orlando M. N. D.,Zboril, Radek,Varma, Rajender S.,Branco, Paula S.
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p. 3494 - 3500
(2014/07/08)
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- Cooperatively assisted N-arylation using organic ionic base-Br?nsted acid combination under controlled microwave heating
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A new synthetic strategy is developed for the construction of C-N bond through the assistance of Br?nsted acid/[DBU][HOAc] without adding any metal catalyst. This is the first efficient SNAr methodology utilizing fluoro, chloro, bromo, and iodoarenes as coupling partners, which offers excellent yield up to 94% within a very short time.
- Singh, Rahul,Allam, Bharat Kumar,Raghuvanshi, Dushyant Singh,Singh, Krishna Nand
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p. 1038 - 1042
(2013/02/23)
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- Synthesis, characterization and catalytic application of some novel binuclear transition metal complexes of bis-(2-acetylthiophene) oxaloyldihydrazone for CN bond formation
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In the present work, synthesis, characterization and catalytic properties of some novel complexes derived from a Schiff base bis-(2-acetylthiophene) oxaloyldihydrazone with various transition metal ions and precursors have been reported. The complexes were characterized by IR, NMR, ESR, electronic and mass spectroscopy, magnetic moments and TGA studies. Molecular structures of the ligand and its Cu(I) complex are determined by single crystal X-ray diffraction. Electronic spectral studies exhibit a 6-coordinated geometry around metal centers for Co(II), Ni(II) and Cu(II) complexes, whereas 4-coordinated geometry for Cu(I) and Zn(II) complexes. ESR spectra indicate a distorted octahedral geometry for Cu(II) complex in DMSO frozen solution. The electro-chemical studies of Ni(II) and Cu(II) complexes reveal a metal based reversible redox behavior. The catalytic activity of the complexes has been demonstrated for the cross-coupling of arylboronic acids with various N-nucleophiles. Ni(II) complex exhibited the maximum impact on catalytic activity with the product yields ranging from 62% to 82%.
- Singh, Divya Pratap,Raghuvanshi, Dushyant S.,Singh,Singh, Vinod P.
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- Triphenyltin chloride as a new source of phenyl group for C-heteroatom and C-C bond formation
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Ph3SnCl is introduced as a very suitable source of phenyl group for coupling with phenols, amines, and thiols in the presence of Cu(OAc)2 in Et3N at room temperature to give aryl ethers, amines, and arylthio ethers in high yields. In addition, the application of Ph3SnCl in the Stille coupling of aryl halides in the presence of Pd(0) catalyst in PEG 400 at 110C is discussed.
- Iranpoor, Nasser,Firouzabadi, Habib,Elham, Etemadi Davan,Rostami, Abed,Nematollahi, Arash
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p. 123 - 130
(2013/10/01)
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- A mild and catalyst-free aromatization using dihydroxylcyclohexanone derivatives as phenyl sources: A new approach to anilines
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A new and efficient protocol for the preparation of N-substituted anilines via an aromatization reaction was developed. 3,5-Dihydroxylcyclohexanone derivatives were used as the sources of the phenyl group and reacted smoothly with primary or secondary amines under mild conditions in the absence of metal catalyst and strong base. A variety of N-substituted anilines were prepared by this method with excellent yields up to 99%. The results indicate that this reaction begins with a nucleophilic addition.
- Luo, Jun,Ji, Enwei,Ye, Jingyuan,Wu, Runze,Qiu, Lei
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p. 4505 - 4508
(2013/08/23)
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- Nickel-mediated N-arylation with arylboronic acids: An avenue to Chan-Lam coupling
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An efficient use of NiCl2·6H2O, for the cross-coupling of arylboronic acids with various N-nucleophiles, has been demonstrated. The method is practical and offers an alternative to the corresponding Cu-mediated Chan-Lam process for the construction of the C-N bond.
- Raghuvanshi, Dushyant Singh,Gupta, Amit Kumar,Singh, Krishna Nand
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supporting information
p. 4326 - 4329
(2012/10/29)
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- NiCl2·6H2O as recyclable heterogeneous catalyst for N-arylation of amines and NH-heterocycles under microwave exposure
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NiCl2·6H2O has been proven to be an effective catalyst for the coupling of amines with aryl iodides without ligand under solvent-free conditions employing microwave irradiation. Reactions cleanly result in coupled products in a short reaction time. The catalyst, being heterogeneous, is recovered by filtration and is recyclable.
- Gupta, Amit Kumar,Tirumaleswara Rao,Singh, Krishna Nand
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experimental part
p. 2218 - 2221
(2012/05/19)
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- A reusable polymer supported copper catalyst for the C-N and C-O bond cross-coupling reaction of aryl halides as well as arylboronic acids
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A simple and industrially viable protocol for C-N and C-O coupling was reported here. The polymer supported heterogeneous copper catalyst was prepared from chloromethyl polystyrene using a simple procedure. O-Arylation of substituted phenols with various aryl halides was achieved using this copper catalyst in DMSO medium. This heterogeneous copper catalyst, also efficiently works for the N-arylation of N-H heterocycles with aryboronic acids in methanol. This catalyst was also effective in amination reaction of primary amines with aryl halides as well as arylboronic acids in DMSO medium. The effects of solvent, base and temperature for the O-Arylation and amination reactions were reported. Further, the catalyst can be easily recovered quantitatively by simple filtration and reused up to several times without sufficient loss of its catalytic activity.
- Islam, Sk.Manirul,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Tuhina,Salam, Noor,Mobarak, Manir
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experimental part
p. 4264 - 4274
(2012/01/06)
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- Palladium- and nickel-catalyzed aminations of aryl imidazolylsulfonates and sulfamates
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A nickel complex derived from dppf, along with NaOt-Bu as the base, allowed for challenging aminations of aryl sulfamates. An improved functional group tolerance is observed in novel palladium-catalyzed aminations of imidazolylsulfonates with rac-BINAP as the ligand.
- Ackermann, Lutz,Sandmann, Rene,Song, Weifeng
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supporting information; experimental part
p. 1784 - 1786
(2011/06/10)
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- Copper-mediated aryl amination: In situ generation of an active copper(I) species
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We have developed novel conditions for copper-mediated aryl amination by using a combination of easy-to-handle and inexpensive Cu(OAc) 2·H2O and phenylhydrazine. Georg Thieme Verlag Stuttgart . New York.
- Komori, Takashi,Satoh, Nobuhiro,Yokoshima, Satoshi,Fukuyama, Tohru
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experimental part
p. 1859 - 1862
(2011/09/15)
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- A reusable polymer supported copper(I) complex for the C-N bond cross-coupling reaction
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The Ullmann coupling of amines with aryl iodide as well as arylboronic acids and N(H)-heterocycles with arylboronic acids has been carried out efficiently using PS-LCu(I) catalyst. The copper complex has been prepared and characterized by using scanning electron microscope (SEM), elemental analysis, atomic absorption spectroscopy (AAS), Thermo gravimetric analysis and spectrometric methods like Fourier transform infrared spectroscopy (FTIR). The effects of various parameters such as temperature, solvent and base on the reaction system were studied. The reusability experiments show that the catalyst can be used five times without much loss in the catalytic activity.
- Islam,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Tuhina, Kazi,Mobarok, Manir
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experimental part
p. 1352 - 1357
(2011/10/12)
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- An efficient recyclable polymer supported copper(II) catalyst for C-N bond formation by N-arylation
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Polymer supported Cu(II) catalyst was prepared, characterized and employed for the N-arylation and amination reaction of N-H heterocycles with aryl halides as well as arylboronic acids to afford the corresponding coupled products in good to excellent yields. This catalyst can be used several times with consistent catalytic activity.
- Islam, Manirul,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Tuhina, Kazi,Mobarok, Manir,Paul, Sumantra,Salam, Noor,Hossain, Dildar
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experimental part
p. 1171 - 1181
(2012/06/18)
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- Addition of aryl cuprates to azides: a novel approach for the synthesis of unsymmetrical diaryl amines
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Aryl and benzyl azides react smoothly with aryl cuprates, generated in situ from aryl magnesium bromide and CuCN in THF to furnish a variety of unsymmetrical diaryl amines in good yields. This is the first report on the synthesis of diarylamines from aryl
- Yadav,Reddy, B.V. Subba,Borkar, Prashant,Reddy, P. Janardhan
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body text
p. 6642 - 6645
(2010/03/01)
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- Iron/copper-cocatalyzed ullmann N,O-arylation using FeCl3, CuO, and rac-1,1′-Binaphthyl-2,2′-diol
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We have developed an efficient and inexpensive bimetallic catalyst FeCl3, CuO, and rac-BINOL that could promote N,O-arylation of aliphatic, arylamines, and phenols. The cross-coupling reaction conditions have high tolerance of various functional groups. This versatile and efficient iron/copper-cocatalyst can widely be used in the synthesis of the compounds containing (aryl)C-N or (aryl)C-O(aryl) bond. Georg Thieme Verlag Stuttgart.
- Wang, Zhe,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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body text
p. 2540 - 2546
(2009/04/12)
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- A mild inter- and intramolecular amination of aryl halides with a combination of CuI and CsOAc
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A unique combination of CuI and CsOAc was found to catalyze aryl amination under mild conditions. The reaction takes place at room temperature or at 90 °C with broad functional group compatibility. The intramolecular reaction was able to form five-, six-, and seven-membered rings with various protecting groups on the nitrogen atom. The scope of the intermolecular amination, as well as its applications to unsymmetrical N,N′-dialkylated phenylenediamines, was investigated.
- Kubo, Tetsuji,Katoh, Chiharu,Yamada, Ken,Okano, Kentaro,Tokuyama, Hidetoshi,Fukuyama, Tohru
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experimental part
p. 11230 - 11236
(2009/04/11)
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- A versatile and efficient ligand for copper-catalyzed formation of C-N, C-O, and P-C bonds: Pyrrolidine-2-phosphonic acid phenyl monoester
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A new and readily available bidentate ligand, namely, pyrrolidine-2- phosphonic acid phenyl monoester (PPAPM), has been developed for the copper-catalyzed formation of C-N, C-O, and P-C bonds, and various N-, O-, and P-arylation products were synthesized in good to excellent yields by using the CuI/PPAPM catalyst system. Addition of the PPAPM ligand greatly increases the reactivity of the copper catalyst, and the resulting versatile and efficient catalyst system is of widespread and practical application in cross-coupling reactions.
- Rao, Honghua,Jin, Ying,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 3636 - 3646
(2008/02/03)
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- An efficient base-free N-arylation of imidazoles and amines with arylboronic acids using copper-exchanged fluorapatite
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(Chemical Equation Presented) N-Arylation of imidazoles and amines with arylboronic acids was accomplished with copper-exchanged fluorapatite (Cu-FAP) in methanol at room temperature. The products N-arylimidazoles and N-arylamines were isolated in good to excellent yields. A variety of arylboronic acids were converted to the corresponding N-arylimidazoles and N-arylamines, demonstrating the versatility of the reaction.
- Kantam, M. Lakshmi,Venkanna, Gopaldasu T.,Sridhar, Chidara,Sreedhar, Bojja,Choudary, Boyapati M.
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p. 9522 - 9524
(2007/10/03)
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- An inexpensive and efficient copper catalyst for N-arylation of amines, amides and nitrogen-containing heterocycles
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An inexpensive and efficient catalyst system has been developed for the N-arylation of nitrogen-containing compounds including a variety of amines, amides, indole and imidazole. This simple protocol uses CuI as the catalyst, commercial available pipecolinic acid as the new ligand, K2CO 3 as the base and DMF as the solvent.
- Guo, Xun,Rao, Honghua,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 2197 - 2202
(2007/10/03)
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- Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2- phosphonate as the new ligand
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We have developed a general, efficient, and inexpensive catalyst system for arylation of amines by using 10 mol % of CuI as the copper source, 20 mol % of diphenyl pyrrolidine-2-phosphonate (DPP) as the ligand, K3PO 4 as the base, and DMF containing 2% water (v/v) as the solvent.
- Rao, Honghua,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 8107 - 8109
(2007/10/03)
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- Microwave-assisted aromatic nucleophilic substitution reaction of chloronitrobenzenes with amines in ionic liquids
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An efficient method for aromatic nucleophilic substitution reaction of chloronitrobenzenes with several substituted amines in environmentally benign, 1-butyl-3-methylimidazolium tetrafluoroborate ionic liquid under microwave irradiation in reduced time period and high yields has been described.
- Angrish, Chetna,Kumar, Anil,Chauhan
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p. 1515 - 1518
(2007/10/03)
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- A new method for the selective amination of 1,3- and 1,4-dinitrobenzenes and protected nitroanilines leading to polyfunctional 1,3- and 1,4-disubstituted anilines
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The addition of functionalized arylmagnesium reagents to dinitrobenzenes and protected nitroanilines at -20°C in THF furnishes after a reductive workup polyfunctional diarylamines in 47-92% yield.
- Sapountzis, Ioannis,Knochel, Paul
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p. 955 - 958
(2007/10/03)
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- Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions
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The first general method for the Pd-catalyzed amination of aryl tosylates and benzenesulfonates was developed utilizing ligand 1, which belongs to a new generation of biaryl monophosphine ligands. In addition, the new catalyst system for the first time enables amidation of aryl arenesulfonates and aqueous amination protocols that do not necessitate the use of cosolvents. The substrate scope has been significantly expanded to include aryl halides containing primary amides and free carboxylic acid groups. In the case of multifunctional substrates, the Pd-catalyzed amination can provide selectivity that is complementary to the Cu-catalyzed C-N bond-forming processes. Copyright
- Huang, Xiaohua,Anderson, Kevin W.,Zim, Danilo,Jiang, Lei,Klapars, Artis,Buchwald, Stephen L.
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p. 6653 - 6655
(2007/10/03)
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- Preparation and pharmacological activities of 10-homolupinanoyl-2-R- phenothiazines
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Pursuing our researches on quinolizidinyl derivatives of phenothiazine and on the ground of antidepressive, diuretic, antianginal and antiarrhythmic activities of several 10-(3-dialkylamino) propionylphenothiazines (as chloracizine, moricizine, etc.), six
- Sparatore,Sparatore
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- DISSOCIATION CONSTANTS OF MONOSUBSTITUTED DIPHENYLAMINES AND AN OPTIMIZED CONSTRUCTION OF ACIDITY FUNCTION
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Eleven monosubstituted diphenylamines have been synthesized, and concentration ratio of the protonated and free bases has been measured in aqueous sulphuric acid in the concentration range 1.0*10-3 to 9.0 mol l-1.An algorithm has been suggested and used for determination of optimized values of pK and H" acidity function within sulphuric acid concentration range 0.05 to 9.0 mol l-1.The results have been compared with literature data and discussed in terms of theory of acidity functions and linear free energy relationships.
- Pytela, Oldrich,Vetesnik, Pavel
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p. 2368 - 2375
(2007/10/02)
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- Micellar Catalysis of the Basic Hydrolysis of Amides. 4. Substituted N,N-Diphenylbenzamides
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The cytalysis of the basic hydrolysis of a series of N-aryl-N-phenylbenzamides (1) and a series of substituted N,N-diphenylbenzamides (2) by micelles of cetyltrimethylammonium bromide (ctab) has been studied.On the basis of the effects of substituents on the aromatic ring attached to the nitrogen atom, a mechanistic change on transfer from water to a micellar environment is proposed.In water the mechanism involves rate-determining solvent-assisted carbon-nitrogen bond breaking (mechanism B), while in the presence of micelles of ctab, a rate-determining attack of hydroxide ion (mechanism C) is proposed.Reasons for mechanistic change are discussed.
- Broxton, Trevor J.,Fernando, Denise R.,Rowe, Jeffrey E.
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p. 3522 - 3525
(2007/10/02)
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