- Mechanistic aspects of copper (II)-catalyzed synthesis of sulfones from sulfinate salts and aryl halides under C-S coupling
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Copper(II)-catalyzed synthesis of sulfones from sulfinate salts and aryl halides was investigated by means of a combination of experiment and DFT calculation. Experimental results demonstrated the wide applicability of the title approach. The reaction mechanisms are revealed by in-situ IR and theoretical study. It reveals remarkable ligand effect the bidentate amine plays in the reaction, that is, it initially activats the C-I bond of iodobenzene so as to enhance the whole catalytic process.
- Ge, Xin,Sun, Fengli,Liu, Xuemin,Chen, Xinzhi,Qian, Chao,Zhou, Shaodong
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- D-Glucosamine as a green ligand for copper catalyzed synthesis of aryl sulfones from aryl halides and sodium sulfinates
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d-Glucosamine is reported for the first time as a green ligand for copper catalyzed coupling of aryl halides and sodium sulfinates, which provides a simple and extremely efficient new route to unsymmetrical diaryl sulfones. The catalytic reaction proceeded in DMSO-H2O at 100°C and gave a variety of aryl sulfones in high yields. The high water solubility of the ligand enables easy catalyst removal. The scope of the method was validated by a single step synthesis of marketed drug zolimidine, a drug used for peptic ulcers, in 65% yield.
- Yang, Ming,Shen, Hongyun,Li, Yuanyuan,Shen, Chao,Zhang, Pengfei
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- Synthesis and characterization of insoluble cobalt(II), nickel(II), zinc(II) and palladium(II) Schiff base complexes: Heterogeneous catalysts for oxidation of sulfides with hydrogen peroxide
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The condensation reaction of 1,2-bis(2'-aminophenoxy)benzene with 2-pyridinecarbaldehyde in a mole ratio of 1:2 gives a new Schiff base ligand (L). Four Schiff base complexes, CoL(NO3)2 (1), NiLCl2 (2), ZnL(NO3)2 (3) and Pd2LCl4 (4) have been prepared by direct reaction of the ligand (L) and appropriate metal salts. The Schiff base ligand (L) has been characterized by IR, 1H NMR and 13C NMR spectroscopy and elemental analysis. Also, all complexes have been characterized by IR and XRD spectroscopy techniques and elemental analysis. The synthesized complexes have very poor solubility in all polar and non-polar solvents such as: H2O, MeOH, EtOH, CH3CN, DMSO, DMF, CHCl3, CH2Cl2, THF, etc; therefore, they have been used as heterogeneous catalysts. Catalytic performance of the complexes was studied in oxidation of thioanisole using hydrogen peroxide (H2O2) as the oxidant. Various factors including the reaction temperature, amount of oxidant and catalyst amount were optimized. The palladium Schiff base complex, Pd2LCl4 (4), shows better catalytic activity than other complexes. Therefore, the Pd(II) Schiff base complex has been used as a catalyst for oxidation of different sulfides to their corresponding sulfones in acetonitrile with hydrogen peroxide as the oxidant. The palladium Schiff base complex, Pd2LCl4 (4), has shown a very good recyclability, up to five times, without any appreciable decreases in catalytic activity and selectivity.
- Menati, Saeid,Amiri Rudbari, Hadi,Askari, Banafshe,Riahi Farsani, Mostafa,Jalilian, Fariba,Dini, Ghasem
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- Interfacing sugar-based surfactant micelles and Cu nanoparticles: A nanoreactor for C-S coupling reactions in water
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A simple and sustainable synergistic catalytic protocol by interfacing nanomicelles and metal nanoparticles (MNPs) is reported for C-S coupling reactions in water. The sugar-based surfactant GluM was synthesized by introducing a PEG chain to stabilize MNPs and self-assembled to form nanomicelles. Cu2O nanoparticles were generated via in situ reduction of copper salt in an aqueous solution of the sugar-based surfactant. The nature of the interaction between nanomicelles and Cu2O nanoparticles was revealed by XPS, XRD, in situ IR, TEM, and 1H NMR. A broad substrate scope with moderate to excellent yields was documented and the recycling of the GluM/Cu aqueous mixture was surprising.
- Ge, Xin,He, Xi,Liu, Xuemin,Qian, Chao,Song, Weili,Yang, Jinguo,Zhou, Shaodong
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- On the important transition of sugar-based surfactant as a microreactor for C-S coupling in water: From micelle to vesicle
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A reversible, temperature-induced micelle-to-vesicle transition of a sugar-based pseudogemini surfactant (C11D12) was employed for copper-catalyzed C-S coupling in water. The phase behavior and morphology of the C11D12 aqueous solution were investigated by DLS and cryo-TEM. The aggregates undergo a series of transitions upon increasing the temperature: spherical micelles were initially transformed into large vesicles, but they eventually transformed into smaller vesicles. The vesicular catalytic protocol accommodates an excellent substrate scope with moderate to high yields. The mechanisms of temperature-induced aggregate transition and vesicular catalysis were elucidated by experimental results and DFT calculations. It was revealed that the charge layer of the vesicle grants stronger nucleophilicity to the PhSO2-Cu-D12Ga intermediate. Furthermore, the aqueous reaction medium can be recycled and reused several times after easily separating the precipitated product.
- Ge, Xin,Lei, Qiuyun,Liao, Xiong,Liu, Xuemin,Song, Weili,Wu, Lei,Wu, Siyuan,Zhou, Shaodong
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- Effective Utilization of in Situ Generated Hydroperoxide by a Co-SiO2@Ti-Si Core-Shell Catalyst in the Oxidation Reactions
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A core-shell catalyst (Co-SiO2@Ti-Si) with cobalt-based SiO2 nanocomposite (Co-SiO2) as the core and Ti-doped mesoporous silica as the shell was designed to catalyze a one-pot reaction of sulfide oxidation with in situ generated hydroperoxide. The catalyst was characterized by SEM, TEM, UV-vis spectroscopy, and XPS, among other methods. Compared to Co-SiO2 and the physical mixture of the two components (Co-SiO2 + Ti-Si), the core-shell catalyst significantly enhanced the reaction rate of the sulfide oxidation. The utilization efficiency of the hydroperoxide was an important factor responsible for the differences in the reaction rates. A further mechanism study showed that the improvement of the efficiency was due to the existence of a coordination pathway. The core-shell structure of a bifunctional catalyst represents a strategy for improving the utilization efficiency of hydroperoxide.
- Liu, Meng,Shi, Song,Zhao, Li,Wang, Min,Zhu, Guozhi,Zheng, Xi,Gao, Jin,Xu, Jie
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- A biradical oxo-molybdenum complex containing semiquinone and: o -aminophenol benzoxazole-based ligands
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We report a new mononuclear molybdenum(iv) complex, MoOLBISLSQ, in which LSQ (2,4-di-tert-butyl o-semibenzoquinone ligand) has been prepared from the reaction of the o-iminosemibenzoquinone form of a tridentate non-innocent benzoxazole ligand, LBIS, and MoO2(acac)2. The complex was characterized by X-ray crystallography, elemental analysis, IR and UV-vis spectroscopy and magnetic susceptibility measurements. The crystal structure of MoOLBISLSQ revealed a distorted octahedral geometry around the metal centre, surrounded by one O and two N atoms of LBIS and two O atoms of LSQ. The effective magnetic moment (μeff) of MoOLBISLSQ decreased from 2.36 to 0.2 μB in the temperature range of 290 to 2 K, indicating a singlet ground state caused by antiferromagnetic coupling between the metal and ligand centred unpaired electrons. Also, the latter led to the EPR silence of the complex. Cyclic voltammetry (CV) studies indicate both ligand and metal-centered redox processes. MoOLBISLSQ was applied as a catalyst for the oxidative cleavage of cyclohexene to adipic acid and selective oxidation of sulfides to sulfones with aqueous hydrogen peroxide. This journal is
- Galindo, Agustín,Jagli?i?, Zvonko,Masoumpour, Marzieh Sadat,Nasibipour, Mina,Safaei, Elham,Wojtczak, Andrzej
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- Electrochemical investigation of the reaction between sodium benzenesulfinate and p-halonitrobenzenes
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Electrochemical evidence suggests that sodium benzenesulfinate reacts with the four p-halonitrobenzenes in a S(N)Ar-reaction, and not in a S(RN)2-reaction, as claimed by other authors.
- Balslev, Henrik,Lund, Henning
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- A reconsideration of the mechanism for the aromatic version of radical nucleophile displacement reactions
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A review of the literature and new experimental data indicate that aromatic radical anions containing leaving groups react with nucleophiles by a bimolecular displacement process.
- Denney, Donald B.,Denney, Dorothy Z.
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- Cu(I)-catalysed coupling of arylsulfinic salts with aryl bromides
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An efficient Cu(I)-catalysed synthesis of diaryl sulfones from arylsulfinic acid salts and aryl bromides in 1,3-dimethyl-2- imidazolidinone at 80 °C in the presence of CuBr and pyridine has been developed. The high-yielding process exhibits significant functional group tolerance and allows for the preparation of a number of diaryl sulfones under mild conditions.
- Peng, Yao
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- A highly active and easily recoverable chitosan@copper catalyst for the C-S coupling and its application in the synthesis of zolimidine
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Aryl sulfones were synthesized using a highly active and easily recoverable heterogeneous Cu catalyst which was prepared by simply stirring an aqueous suspension of chitosan in water with copper salts. The chitosan@copper catalyst catalyzed the coupling reactions of aryl halides with sodium sulfinates to readily give the corresponding sulfones in good to excellent yields. The highly active catalyst can be reused many times without losing its catalytic activity. In addition, by using this protocol, the marketed drug zolimidine (antiulcer) could be synthesized easily. This journal is the Partner Organisations 2014.
- Shen, Chao,Xu, Jun,Yu, Wenbo,Zhang, Pengfei
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- Highly selective and efficient oxidation of sulfides with hydrogen peroxide catalyzed by a chromium substituted Keggin type polyoxometalate
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The catalytic oxidation of sulfides into the corresponding sulfones by a chromium substituted Keggin type polyoxometalate, (TBA)4[PW 11CrO39]·3H2O, was achieved using mild reaction conditions. Excellent yields were obtained using four equivalents of 30% H2O2. Under these reaction conditions, the sulfide group was highly reactive and other functional groups such as hydroxyl or a double bond were unaffected. Using a commercially available, eco-friendly, and cheap oxidant, mild reaction conditions, operational simplicity, practicality, short reaction times, high to excellent yields, and excellent chemoselectivity are some of the advantages of this catalytic system.
- Afrasiabi, Roozbeh,Farsani, Mostafa Riahi,Yadollahi, Bahram
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- Solvent free oxidation of sulfides to sulfones by H2O2 in the presence of chromium substituted polyoxometalate as catalyst
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Solvent-free oxidation of sulfides into sulfones by 30% hydrogen peroxide has been achieved using chromium substituted Keggin type polyoxometalate under mild reaction conditions in 94-100% yield. This catalytic system showed excellent activity in the oxidation of sulfide groups. The other active functional groups such as hydroxyl and C=C bond have been tolerated.
- Afrasiabi, Roozbeh,Jalilian, Fariba,Yadollahi, Bahram,Farsani, Mostafa Riahi
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- Sulfoxide and Sulfone Synthesis via Electrochemical Oxidation of Sulfides
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The oxidation of diaryl sulfides and aryl alkyl sulfides to the corresponding sulfoxides and sulfones under electrochemical conditions is reported. Sulfoxides are selectively obtained in good yield under a constant current of 5 mA for 10 h in DMF, while sulfones are formed as the major product under a constant current of 10 or 20 mA for 10 h in MeOH. The oxygen of both the sulfoxide and sulfone function is derived from water.
- Lee, Sunwoo,Park, Jin Kyu
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p. 13790 - 13799
(2021/10/12)
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- Mo(VI) complex catalysed synthesis of sulfonees and their modification for anti-HIV activities
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An efficient method for the synthesis of sulfones has been developed using sugar derived cis-dioxo molybdenum(VI) complex as catalyst and urea hydrogen peroxide as oxygen source. Present method is highly specific for sulfide oxidation irrespective of presence of alkene and aldehyde groups in the same molecule. Synthesis of fifteen sulfones have been reported with 82–98% isolated yields and the catalyst has been reused five times without any loss in its activity. 2-(Phenylsulfonyl)aniline has been condensed with eight different aromatic aldehydes and the products are being explored for HIV-1 reverse transcriptase inhibition activities.
- Madduluri, Vimal Kumar,Baig, Noorullah,Chander, Subhash,Murugesan, Sankaranarayanan,Sah, Ajay K.
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- Hantzsch Ester as a Visible-Light Photoredox Catalyst for Transition-Metal-Free Coupling of Arylhalides and Arylsulfinates
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Diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (HEH) has been utilized as a visible-light photoredox catalyst for the cross coupling of arylhalides and arylsulfinates without transition metal, sacrificial agent, and mediator. This method is compatible with various functional groups and provides diaryl sulfones in good to high yields. Mechanistic studies indicate that this reaction undergoes the stepwise light irradiation of HE?, single electron transfer (SET) in donor–acceptor complex (DAC) from *HE? to arylhalide, trapping of aryl radical with sulfinate, and SET oxidation of sulfone radical anion by HE. to sulfone by the DAC method.
- Zhu, Da-Liang,Wu, Qi,Li, Hai-Yan,Li, Hong-Xi,Lang, Jian-Ping
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supporting information
p. 3484 - 3488
(2020/03/05)
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- A designed bi-functional sugar-based surfactant: Micellar catalysis for C-X coupling reaction in water
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A bi-functional sugar-based surfactant ALA14 was designed as the ligand and micelle constructor and demonstrated to promote the copper-catalyzed C-X coupling reaction in water. The nature of this micelle, formed by sugar-based surfactants, was investigated with CMC, DLS, and TEM, by which encapsulation and aggregation of the substrates in micelles were verified. Additionally, it was addressed by 1H-NMR analysis that the enrichment position of the substrates is in the lipophilic alkyl chain. Finally, moderate to excellent yields of the aimed products were obtained in this work. This remarkably simple strategy expanded the scope of C-X coupling reaction in water; most notably, both water and ALA14 can be recycled and reused.
- Ge, Xin,Zhang, Shihui,Chen, Xinzhi,Liu, Xuemin,Qian, Chao
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supporting information
p. 2771 - 2776
(2019/06/13)
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- SUBSTITUTED PHENYL SULFONYL PHENYL TRIAZOLE THIONES AND USES THEREOF
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The present disclosure relates to substituted phenyl sulfonyl phenyl triazole thiones, pharmaceutical compositions containing them, and methods of using them.
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- METHOD OF TREATING A CONDITION ASSOCIATED WITH NEURODEGENERATION USING INHIBITORS OF OAT3
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The present disclosure relates to therapeutic agents that may be useful in treatment and prophylaxis of neurodegenerative disorders and/or neural inflammation.
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- Regiospecific Cleavage of S-N Bonds in Sulfonyl Azides: Sulfonyl Donors
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Sulfonyl azides have been widely used as sulfonamido, diazo, and azido donors, as well as all-nitrogen 1,3-dipoles donors in synthetic chemistry. Here, the sulfonyl azides were used as efficient sulfonyl donors, which is very unusual. Trifluoromethanesulfonic acid-induced formation of the sulfonyl cation reactive species from sulfonyl azides was developed and used for the first time to couple various inactivated arenes to prepare sulfones at ambient temperature.
- Zhang, Zhiguo,Wang, Songnan,Zhang, Yong,Zhang, Guisheng
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p. 3919 - 3926
(2019/03/29)
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- Efficient Ullmann C-X coupling reaction catalyzed by a recoverable functionalized-chitosan supported copper complex
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Three different types of functionalized-CS were prepared and anchored with copper salts for use as the catalyst for the Ullmann C-X coupling reaction. The Schiff-basic chitosan supported copper complex (PCCS@CuI) exhibits the highest catalytic activity. The structure of the catalyst was characterized by FTIR spectroscopy, TG, XRD, SEM, EDS and XPS. This catalyst exhibited high applicability for the C-N and C-S coupling reactions, in which good to excellent yields were obtained. Its easy separation, good reusability and stability were notable.
- Liu, Xuemin,Chang, Shuo,Chen, Xinzhi,Ge, Xin,Qian, Chao
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supporting information
p. 16013 - 16020
(2018/10/04)
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- Reusable BNPs-SiO2@(CH2)3NHSO3H-catalysed selective oxidation of sulfides to sulfones
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Reusable boehmite nanoparticles–silica–NHSO3H (BNPs-SiO2@(CH2)3NHSO3H) was found to be an efficient heterogeneous nanocatalyst for the selective oxidation of sulfides to sulfones in the presence of H2O2. Excellent yields, easy and quick isolation of products, short reaction times and excellent selectivity are the main advantages of this method. The catalyst was characterized using Fourier transform infrared spectroscopy, energy-dispersive X-ray analysis, X-ray diffraction, and transmission and scanning electron microscopies.
- Bahrami, Kiumars,Khodamorady, Minoo
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- Nickel-Catalyzed Synthesis of Diaryl Sulfones from Aryl Halides and Sodium Sulfinates
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A novel nickel-catalyzed cross-coupling of sulfinic acid salts with aryl halides is described. The reaction provides access to various diaryl sulfones in moderate to excellent yields. A broad range of functional groups and heteroaromatic compounds is tolerated under the reaction conditions.
- Liu, Nai-Wei,Liang, Shuai,Margraf, Natalie,Shaaban, Saad,Luciano, Vanessa,Drost, Marcella,Manolikakes, Georg
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supporting information
p. 1208 - 1210
(2018/03/21)
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- A practical synthesis of aryl sulfones via cross-coupling of sulfonyl hydrazides with aryltriazenes using copper/ionic liquid combination
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A new and efficient approach adopting copper-catalyzed cross-coupling of sulfonyl hydrazides with aryltriazenes has been developed to synthesize aryl sulfones using Br?nsted acidic ionic liquid as promoter under ambient conditions. The process employs stable and easy to handle reacting partners, and is endowed with broad substrate scope.
- Pandey, Anand Kumar,Kumar, Saurabh,Singh, Rahul,Singh, Krishna Nand
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supporting information
p. 6704 - 6709
(2018/10/15)
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- Efficient synthesis of aliphatic sulfones by Mg mediated coupling reactions of sulfonyl chlorides and aliphatic halides
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Sulfonyl chlorides were reduced to anhydrous sulfinate salts with magnesium under sonication. These sulfinates were alkylated to sulfones with alkyl chlorides in the presence of catalytic sodium iodide under sonication. A variety of aliphatic sulfones was efficiently prepared by this one-pot two-step procedure.
- Fu, Ying,Xu, Qin-Shan,Li, Quan-Zhou,Du, Zhengyin,Wang, Ke-Hu,Huang, Danfeng,Hu, Yulai
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supporting information
p. 2841 - 2845
(2017/04/03)
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- METHODS OF INHIBITING BACTERIAL VIRULENCE AND COMPOUNDS RELATING THERETO
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The present invention relates to compounds and methods for the treatment of bacterial infections. Because their mechanism of action does not involve killing of bacteria or inhibiting their growth, the potential for these compounds to induce drug resistance in bacteria is minimized. Through inhibiting bacterial virulence, the present invention provides a novel means of treating bacterial infections.
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Paragraph 0210
(2017/01/31)
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- Application of sodium titanate nanotubes doped with vanadium (VNaTNT) as a heterogeneous catalyst for oxidation of sulfides at room temperature
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A heterogeneous titanate nanotube (TNT) catalyst containing TiO2, Na, and V has been synthesized and used in the chemoselective oxidation of sulfides to the corresponding sulfoxides in the presence of 30% H2O2 in water. Some of the advantages of our method include excellent yields, heterogeneous conditions, simplicity, compatibility with a variety of functionalities, and ease of isolation of the products. Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, transmission electron microscopy, and N2 adsorption were used for structural and textural characterization of the catalyst (VNaTNT).
- Dadvar, Mohammad Ali,Fazaeli, Razieh
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p. 494 - 501
(2016/04/20)
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- Asymmetric diaryl sulfone compound and its preparation method
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The invention relates to an asymmetric diaryl sulfone compound and a preparation method thereof, and discloses diaryl sulfone into which aryl fluoborate catalyzed by cuprous chloride participates at room temperature, and a preparation method thereof. Available nontoxic aryl sulfinic acid sodium is selected as a substrate, and a low-cost reaction system is selected to develop coupling reaction of aryl sulfinic acid sodium and aryl potassium fluoborate catalyzed by cuprous chloride, so as to synthesize asymmetric diaryl sulfone. The diaryl sulfone synthesis method is economic and effective, mild in condition, short in reaction time, high in reaction yield and low in cost, and has good practicability and economic value.
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Paragraph 0036-0038
(2017/04/27)
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- Kinetic investigation on the highly efficient and selective oxidation of sulfides to sulfoxides and sulfones with t-BuOOH catalyzed by La2O3
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The selective oxidation of various sulfides to sulfoxides by a simple, efficient, and environmentally benign method is of prime focus. In this paper, we have explored a highly efficient protocol for the oxidation of alkyl aryl sulfides to sulfoxides with high selectivities catalyzed by La2O3 in the presence of 70% t-BuOOH solution (water). We obtained predominantly the monooxygenated product. The over oxidation of sulfides to sulfones was not observed under these conditions. The resulting products are obtained in good to excellent yields within a reasonable time without the use of ligands and other additives. The epoxidation of the double bond as well as allylic oxidation are not observed with allyl sulfides. Sulfones can be obtained quantitatively by altering the reaction conditions. The surface morphology and the catalyst reusability were verified by XRD, AFM and SEM techniques. The surface area of the La2O3 was measured using BET isotherms.
- Mandal, Mrinmay,Chakraborty, Debashis
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p. 12111 - 12122
(2015/02/19)
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- Tungstate supported on periodic mesoporous organosilica with imidazolium framework as an efficient and recyclable catalyst for the selective oxidation of sulfides
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Abstract A catalyst based on immobilization of tungstate ions (WO42-) inside the mesochannels of periodic mesoporous organosilica comprising bridged ionic liquid (1,3-bis(3-trimethoxysilylpropyl)imidazolium chloride) has been synthesized and characterized. This catalyst was then employed for the selective oxidation of organic sulfides to the corresponding sulfoxides or sulfones. The final synthesized catalyst was characterized by various techniques such as nitrogen sorption analysis, transmission electron microscopy, and thermogravimetric analysis. The catalyst was also applied to the selective oxidation of sulfides containing readily oxidizable functional groups such as hydroxyl, allylic, and even challenging aliphatic sulfides. Interestingly, it was found that on changing the reaction medium from aqueous methanol to aqueous acetonitrile, the product selectivity was changed successfully from sulfoxide to sulfone with good to excellent yields. Moreover, the catalyst can also be recovered and reused efficiently in nine subsequent reaction cycles without any remarkable decrease in the catalyst activity and selectivity.
- Karimi, Babak,Khorasani, Mojtaba,Bakhshandeh Rostami, Fatemeh,Elhamifar, Dawood,Vali, Hojatollah
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p. 990 - 999
(2015/06/08)
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- Cobalt(II), copper(II), zinc(II) and palladium(II) Schiff base complexes: Synthesis, characterization and catalytic performance in selective oxidation of sulfides using hydrogen peroxide under solvent-free conditions
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An asymmetric bidentate Schiff-base ligand (HL: 2-tert-butyliminomethyl-phenol) was prepared from the reaction of salicylaldehyde and tert-butylamine. Cobalt(II), copper(II), zinc(II) and Pd(II) complexes, CoL2, CuL2, ZnL2 and PdL2, were synthesized from the reaction of CoCl2·6H2O, CuCl2·2H2O, Zn(NO3)2·6H2O and PdCl2 with the bidentate Schiff base ligand HL in methanol. The ligand and its metal complexes were characterized by elemental analysis (CHN), FT-IR and UV-Vis spectroscopy. In addition, 1H and 13C NMR techniques were employed for characterization of the ligand (HL) and the diamagnetic complexes (ZnL2 and PdL2). The molecular structures of all the complexes were determined by the single crystal X-ray diffraction technique. The crystallographic data reveal that in all the complexes the metal centers are four-coordinated by two phenolate oxygen and two imine nitrogen atoms of two Schiff base ligands. The geometry around the metal center in the CoL2, CuL2 and ZnL2 complexes is a distorted tetrahedral and for PdL2 it is square-planar. The catalytic activity of these complexes has been evaluated for the selective oxidation of sulfides with the green oxidant 35% aqueous H2O2 under solvent free conditions. For all the catalysts, using optimized reaction conditions, different sulfides were converted to the corresponding sulfones. ZnL2 showed a higher catalytic performance for the oxidation of the different sulfides to the corresponding sulfones.
- Khorshidifard, Mahsa,Rudbari, Hadi Amiri,Askari, Banafshe,Sahihi, Mehdi,Farsani, Mostafa Riahi,Jalilian, Fariba,Bruno, Giuseppe
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- A PROCESS FOR THE SYNTHESIS OF ARYL SULFONES
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The present patent discloses a novel, efficient and transition-metal-free room temperature single step process for synthesis of aryl sulfones and substituted aryl sulfones starting from aryl substrates.
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Page/Page column 10; 12; 18; 19
(2015/06/25)
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- Synthesis of diaryl sulfones at room temperature: Cu-catalyzed cross-coupling of arylsulfonyl chlorides with arylboronic acids
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An efficient and convenient method for the synthesis of diaryl sulfones was developed through the Cu-catalyzed cross-couplings of arylsulfonyl chlorides and arylboronic acids at room temperature in open air. This method is characterized by the use of inexpensive and readily available catalyst and substrates, mild reaction conditions, wide functionality tolerance, short reaction times for most substrates, and moderate to good yields. Stitch it up with copper: An efficient and convenient method for the synthesis of diaryl sulfones was developed through the Cu-catalyzed cross- couplings of arylsulfonyl chlorides and arylboronic acids at room temperature in open air.
- Hu, Feng,Lei, Xiangyang
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p. 1539 - 1542
(2015/05/27)
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- Magnetically separable copper ferrite nanoparticles-catalyzed synthesis of diaryl, alkyl/aryl sulfones from arylsulfinic acid salts and organohalides/boronic acids
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A recyclable, inexpensive, non-toxic and environmentally benign catalytic system comprised of magnetically separable copper ferrite (CuFe 2O4) nanoparticles has been developed for the synthesis of diaryl, alkyl/aryl sulfones. Arylsulfinic acid salts are coupled with various alkyl/aryl halides/boronic acids to afford the corresponding diaryl, alkyl/aryl sulfones in good to excellent yields under the identical catalytic system. A wide range of functional group tolerance, with facile recovery of the catalyst by application of an external magnetic field, and consistently high catalytic efficiency for five consecutive cycles render the protocol operationally attractive.
- Srinivas,Rawat, Vikas S.,Konda, Kavitha,Sreedhar, Bojja
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p. 805 - 817
(2014/04/03)
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- Copper-catalysed coupling of aryl tosylates with sodium arylsulfinates
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Diaryl sulfones derivatives were easily synthesised from aryl tosylates and sodium arylsulfinates in high yields using [Cu(CH3CN)4]PF6 as catalyst. The transformation is efficient, simple and the starting materials are readily available.
- Wang, Chunjie,Zhang, Hui,Li, Zhiwei,Wang, Ziyun
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p. 639 - 642
(2015/02/02)
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- Transition-metal-free C-S bond formation: A facile access to aryl sulfones from sodium sulfinates via arynes
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Sulfones have been attractive targets for synthetic organic chemists owing to their immense applications in medicinal, material, and synthetic chemistry. In this context, an efficient transition-metal-free process has been demonstrated, wherein a broad range of alkyl/aryl/heteroaryl sodium sulfinates react with varyingly substituted aryne precursors (o-silyl aryl triflates) under mild reaction conditions to afford structurally diverse sulfones in good to excellent yields.
- Pandya, Virat G.,Mhaske, Santosh B.
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supporting information
p. 3836 - 3839
(2014/08/05)
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- CuI catalyzed sulfonylation of organozinc reagents with sulfonyl halides
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In this study, a facile CuI catalyzed synthesis of sulfones involving a nucleophilic addition of functionalized organozinc reagents to organic sulfonyl chlorides is realized. This reaction proceeds efficiently at room temperature, giving rise to various functional group substituted sulfones, generally in moderate to high yields. The method provides a novel, simple, and promising strategy for functionalized sulfone synthesis in the research field of sulfur chemistry. the Partner Organisations 2014.
- Fu, Ying,Zhu, Wenbo,Zhao, Xingling,Huegel, Helmut,Wu, Zhouqiang,Su, Yuhu,Du, Zhengyin,Huang, Danfeng,Hu, Yulai
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supporting information
p. 4295 - 4299
(2014/06/23)
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- Diaryl sulfones synthesis with aryltrifluoroborates and aryl sulfinic salts under mild conditions
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CuI-catalysed cross-coupling reactions of various aryltrifluoroborates with aryl sulfinic salts have been achieved in good yields. A new efficient method is described for the conversion of potassium aryltrifluoroborates into diaryl sulfones. The reported reactions are tolerant to common functional groups regardless of whether they are electron-rich or electron-deficient, making this transformation an attractive alternative to traditional approaches.
- Zhang, Wei,Li, Ke,Zhao, Baoli
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p. 269 - 271
(2014/06/09)
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- Selectivity adjustment of SBA-15 based tungstate catalyst in oxidation of sulfides by incorporating a hydrophobic organic group inside the mesochannels
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A novel heterogeneous catalyst system comprising tungstate ions embedded into the hydrophobic mesochannels of SBA-15 was found to exhibit significant selectivity enhancement in oxidation of sulfides in water or water/CH 3CN using 30% H2O2. Our studies demonstrated that the presence of an n-octyl group in the interior of nanospaces of our catalyst system provides a hydrophobic/hydrophilic region in the mesochannels of the catalyst where the active tungstate species are located and in turn results in at least three distinct important features. First of all, the catalyst comprising the n-octyl group shows much better water tolerance than the catalysts not having hydrophobic organic moieties. Moreover, the nonproductive decomposition of H2O2 was significantly inhibited in the present catalyst system. The present catalyst system also offers an unprecedented selectivity changeover depending on the hydrophobic nature of the initial sulfides and/or the utilized solvent mixture. While high yields and excellent selectivities toward the corresponding sulfoxide were obtained in the oxidation of less hydrophobic sulfides in H2O as a reaction solvent, the selectivity pattern was shifted toward sulfones in the case of using more hydrophobic sulfides as substrates. On the other hand, in CH3CN/ H2O (1:1) as the reaction solvent, almost all of the studied sulfides were selectively oxidized to the corresponding sulfoxide in high yields. On the basis of several compelling observations, we have proposed a synergistic model to explain the origin of the observed selectivities. The catalyst was respectively recovered and reused in five and seven successive reaction runs in water and water/CH3CN, respectively, with only a slight decrease of reactivity.
- Karimi, Babak,Khorasani, Mojtaba
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p. 1657 - 1664
(2013/07/26)
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- Discovery of potent and efficacious urea-containing nicotinamide phosphoribosyltransferase (NAMPT) inhibitors with reduced CYP2C9 inhibition properties
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Potent, reversible inhibition of the cytochrome P450 CYP2C9 isoform was observed in a series of urea-containing nicotinamide phosphoribosyltransferase (NAMPT) inhibitors. This unwanted property was successfully removed from the described inhibitors throug
- Gunzner-Toste, Janet,Zhao, Guiling,Bauer, Paul,Baumeister, Timm,Buckmelter, Alexandre J.,Caligiuri, Maureen,Clodfelter, Karl H.,Fu, Bang,Han, Bingsong,Ho, Yen-Ching,Kley, Nikolai,Liang, Xiaorong,Liederer, Bianca M.,Lin, Jian,Mukadam, Sophie,O'Brien, Thomas,Oh, Angela,Reynolds, Dominic J.,Sharma, Geeta,Skelton, Nicholas,Smith, Chase C.,Sodhi, Jasleen,Wang, Weiru,Wang, Zhongguo,Xiao, Yang,Yuen, Po-Wai,Zak, Mark,Zhang, Lei,Zheng, Xiaozhang,Bair, Kenneth W.,Dragovich, Peter S.
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p. 3531 - 3538
(2013/07/28)
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- Synthesis of substituted diphenyl sulfones and their structure-activity relationship with the antagonism of 5-HT6 receptors
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Substituted diphenyl sulfones (10a-n) were synthesised, and the structures were confirmed by NMR, LC-MS and X-ray crystallography. Their antagonistic activities towards 5-HT6 receptor were assessed in a cell-based functional assay. Diphenyl sulfone 10a, in spite of being the smallest and simplest known sulfonyl-containing 5-HT6R antagonist, showed a strong potency (Ki = 1.6 μM). Its derivative with a methylamine substituent, 10g (N-methyl-2-(phenylsulfonyl)aniline), was ~66-times as active as diphenyl sulfone (Ki = 24.3 nM). Addition of a piperazinyl moiety in the para-position relative to the sulfonyl group in compound 10m (N-methyl-2-(phenylsulfonyl)-5-piperazin-1-ylaniline) led to a further 150-fold increase in potency (Ki = 0.16 nM) to block the serotonin-induced response of HEK-293 cells that were stably transfected with the human recombinant 5-HT6 receptor.
- Ivachtchenko, Alexandre,Golovina, Elena,Kadieva, Madina,Mitkin, Oleg,Tkachenko, Sergei,Okun, Ilya
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p. 4614 - 4627
(2013/07/26)
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- Metal-free synthesis of diaryl sulfones from arylsulfinic acid salts and diaryliodonium salts
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An efficient, high-yielding, and transition-metal-free synthesis of diaryl sulfones from arylsulfinic acid salts and diaryliodonium salts has been developed. The mild reaction conditions tolerate a range of functional groups, and unsymmetrical diaryliodonium salts show high chemoselectivity.
- Umierski, Natalie,Manolikakes, Georg
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supporting information
p. 188 - 191
(2013/03/28)
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- Host (aluminum incorporated mesocellulous silica foam (Al-MCF))-guest (tungsten polyoxometalate) nanocomposite material: An efficient and reusable catalyst for selective oxidation of sulfides to sulfoxides and sulfones
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A green, efficient and selective approach for the oxidation of sulfides to sulfoxides and sulfones with H2O2 at room temperature is reported. The reaction is performed in the presence of tungstophosphoric acid (PW12) supported on an aluminum incorporated mesocellulous silica foam (Al-MCF) (via both: the impregnation and encapsulation methods), as heterogeneous and reusable catalysts. The structural and textural characterizations of these catalysts were done using FTIR, X-ray diffraction, N2 adsorption-desorption and TEM.
- Fazaeli, Razieh,Aliyan, Hamid,Ahmadi, Mohammad Ali,Hashemian, Saeedeh
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- A mild and efficient synthesis of aryl sulfones from aryl chlorides and sulfinic acid salts using microwave heating
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The CuCl-catalyzed coupling of aryl chlorides and sulfinic acid salts provides a simple and extremely efficient route to unsymmetrical aryl sulfones in high to excellent yields under microwave irradiation within 3-30 minutes. Georg Thieme Verlag Stuttgart · New York.
- Yuan, Yan-Qin,Guo, Sheng-Rong
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supporting information; experimental part
p. 2750 - 2756
(2011/12/04)
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- Anion-functionalized ionic liquids enhance the cui-catalyzed cross-coupling reaction of sulfinic acid salts with aryl halides and vinyl bromides
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An easily accessible, anion-functionalized ionic liquid, 1-ethyl-3-methylimidazolium (S)-2-amino-3-methylbutyric acid salt, [emim][Val], has been demonstrated to be an efficient additive for the CuI-catalyzed coupling reaction of sulfinic acid salts with aryl iodides, aryl bromides and vinyl bromides, leading to the formation of sulfones in good yields. Georg Thieme Verlag Stuttgart.
- Bian, Ming,Xu, Fada,Ma, Cheng
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p. 2951 - 2956
(2008/03/13)
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- Caro's acid supported on silica gel. IV. Facile synthesis of sulfones by the oxidation of various sulfides in aprotic solvent
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Oxidation of sulfides with Caro's acid supported on silica gel in acetonitrile gave sulfones in high to excellent yields under mild condition.
- Lakouraj, Moslem M.,Movassagh,Ghodrati
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p. 847 - 850
(2007/10/03)
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- 1,2-Diarylpyrroles as potent and selective inhibitors of cyclooxygenase- 2
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Series of 1,2-diarylpyrroles has been synthesized and found to contain very potent and selective inhibitors of the human cyclooxygenase-2 (COX-2) enzyme. The paper describes short and practical syntheses of the target molecules utilizing the Paal-Knorr reaction. Electrophilic substitution on 1 proceeds in a regioselective fashion, and the method was used to generate a number of tetrasubstituted pyrroles. Detailed SAR on the series has been studied by modifications of the aryl rings and the substituents in the pyrrole ring. Diarylpyrrole 1 is a very potent (COX-2, IC50 = 60 nm) and selective (COX-1/COX-2 = > 1700) inhibitor whereas the isomeric 2 is completely inactive against COX-2. Modifications of the substituents on the fluorophenyl ring in 1 yields very potent inhibitors of COX-2 (IC50 = 40- 80 nm) with excellent selectivity(1200 to >2500) vs COX-1, Analog 20 containing a sulfonamide group is an excellent inhibitor of COX-2 with an IC50 of 14 nm. Tetrasubstituted pyrroles containing groups such as COCF3, SO2CF3, or CH2OAr at position 3 in the pyrrole ring give excellent inhibitors (COX-2, IC50 = 30-120 nm). In vivo testing in the carrageenan- induced paw edema model in the rat establishes that the 1,2-diarylpyrroles are orally active antiinflammatory agents. Compound 3 is the most potent inhibitor of edema with an ED50 of 4.7 mpk.
- Khanna, Ish K.,Weier, Richard M.,Yu, Yi,Collins, Paul W.,Miyashiro, Julie M.,Koboldt, Carol M.,Veenhuizen, Amy W.,Currie, Jerry L.,Seibert, Karen,Isakson, Peter C.
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p. 1619 - 1633
(2007/10/03)
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- Photoelectrochemical reduction of meta-halonitrobenzenes and related species
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Dual photo- and electro-chemical activation of m-chloronitrobenzene and m-bromonitrobenzene in acetonitrile solution leads to halide loss through a photo-ECE mechanism.This proceeds via absorption of visible light by the radical anions .-, which is followed by fragmentation forming the .C6H4NO2 aryl radical.The latter reacts with the solvent system forming nitrobenzene which is further reduced at the electrode with the generation of .-. reduction of m-iodonitrobenzene leads to iodide loss without the need for irradiation.However, this process is accelerated by visible light.In contrast the dual activation of p-cyanonitrobenzene, p-dinitrobenzene, phenyl 4-nitrophenyl sulfone, methyl 4-nitrophenyl sulfone, phenyl 4-nitrophenyl sulfoxide or methyl 4-nitrophenyl sulfoxide failed to induce the leaving of any substituent suggesting that the process may be selective to halo-compounds.
- Compton, Richard G.,Dryfe, Robert A. W.,Eklund, John C.,Page, Stephen D.,Hirst, Judy,et al.
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p. 1673 - 1678
(2007/10/02)
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- Dihalomethylation of Nitroarenes via Vicarious Nucleophilic Substitution of Hydrogen with Trihalomethyl Carbanions
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Trichloro- and tribromomethyl carbanions generated by deprotonation of haloforms with potassium tert-butoxide in a THF-DMF mixture at ca. -70 deg C react with a variety of carbocyclic and heterocyclic nitroarenes according to the vicarious nucleophilic substitution scheme.The reaction provides an efficient and convenient way for the direct introduction of dihalomethyl substituents ortho and para to the nitro group, which in turn can be hydrolyzed to produce nitroaryl aldehydes.
- Makosza, M.,Owczarczyk, Z.
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p. 5094 - 5100
(2007/10/02)
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