- NMR Study of Substituent Effects in 4-Substituted and 4,4'-Disubstituted Diphenyl Sulphides
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The proton and carbon NMR spectra of nine 4-X-diphenyl sulphides (series 1), seven 4-X-4'-NO2-diphenyl sulphides (series 2) and eight 4,4'-X2-diphenyl sulphides (series 3) have been obtained.Correlation of the 13C chemical shifts with the appropriate substituent chemical shifts (SCS) for monosubstituted benzenes (Lynch plots) show an enhancement of substituent effect at C-1 (carbon para to the substituent) in series 1 ans 2, but not in series 3.The carbons of the unsubstituted ring in series 1 also correlate with Cp-SCS, with slopes of less than unity; correlation for C-1' has a negative slope.Dual substituent parameter (DSP) correlations of the 13C chemical shifts with ?I/?oR are good to exellent for all the carbons of series 1 compounds, except those ortho to the substituent X.The carbons meta to the substituent X correlate well, but with negative values for ρI and ρR, although showing a scattered Lynch plot.Similar correlations are found with some carbon shifts in series 2, and with C-1 shifts in series 3.It is concluded that (a) reverse resonance effects are operative at the position meta to the variable substituent by virtue of the sulphur substituent ortho to that carbon; (b) there is transmission of inductive (field) and resonance effects from one aryl ring to the other, except when both rings carry substituents of the same electronic character (series 3); (c) there is some evidence for ?-polarization in the unsubstituted phenyl ring of series 1 compounds.Key words 1H NMR 13C NMR Diphenyl sulphides substituent effects
- Chandrasekaran, R.,Perumal, S.,Wilson, D.A.
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- Synthesis of diaryl sulfides based on copper-doped OMS-2
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We describe a practical protocol for efficiently preparing diaryl sulfide compounds using Cu–OMS-2 as the catalyst. Cu–OMS-2 originates from manganese oxide octahedral molecular sieves modified with copper ions and catalyzes the C–S coupling reaction of substituted thiophenols and aryl halides. This protocol has the advantages of environmental friendliness, simple operation, high yields, good tolerance of functional groups, and the Cu–OMS-2 catalytic material can be recycled several times.
- Yu, Shao-Qiang,Liu, Na,Liu, Ming-Guo,Wang, Long
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p. 237 - 241
(2020/11/30)
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- Optimization of a urea-containing series of nicotinamide phosphoribosyltransferase (NAMPT) activators
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NAD+ is a crucial cellular factor that plays multifaceted roles in wide ranging biological processes. Low levels of NAD+ have been linked to numerous diseases including metabolic disorders, cardiovascular disease, neurodegeneration,
- Pinkerton, Anthony B.,Sessions, E. Hampton,Hershberger, Paul,Maloney, Patrick R.,Peddibhotla, Satyamaheshwar,Hopf, Meghan,Sergienko, Eduard,Ma, Chen-Ting,Smith, Layton H.,Jackson, Michael R.,Tanaka, Jun,Tsuji, Takashi,Akiu, Mayuko,Cohen, Steven E.,Nakamura, Tsuyoshi,Gardell, Stephen J.
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- Nucleophilic aromatic substitution reactions under aqueous, mild conditions using polymeric additive HPMC
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The use of the inexpensive, benign, and sustainable polymer, hydroxypropyl methylcellulose (HPMC), in water enables nucleophilic aromatic subsitution (SNAr) reactions between various nucleophiles and electrophiles. The mild reaction conditions facilitate a broad functional group tolerance that can be utilized for subsequent derivatization for the synthesis of pharmaceutically relevant building blocks. The use of only equimolar amounts of all reagents and water as reaction solvent reveals the greenness and sustainability of the methodology presented herein.
- Ansari, Tharique N.,Borlinghaus, Niginia,Braje, Leon H.,Braje, Wilfried M.,Handa, Sachin,Ogulu, Deborah,Wittmann, Valentin
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supporting information
p. 3955 - 3962
(2021/06/17)
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- Highly active mesoionic chalcogenone zinc(II) derivatives for C-S cross-coupling reactions
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The first mesoionic heavier chalcogenones, L1-L3 [L1 = 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-selone; L2 = 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-thione; L3 = 1-(benzyl)-2-3(methyl)-4-phenyltriazolin-5-selone], were isolated and characterised. Density functional theory was used to obtain insights into the σ donor and π accepting nature of mesoionic chalcogenones. Using these new ligands, a series of the first zinc(ii) mesoionic chalcogenone complexes were isolated. Three mono nuclear zinc(ii) chalcogenone complexes, [(L1)Zn(Cl)2(HOMe)] (1), [(L2)Zn(Cl)2(HOMe)] (3) and [(L2)Zn(Br)2(HOMe)] (4), and two dinuclear zinc complexes, [(L1)Zn(Br)(μ2-Br)]2 (2) and [(L3)Zn(Br)(μ2-Br)]2 (5), containing mesoionic thione and selone ligands were synthesized and characterised. These new complexes 1-5 represent the first structurally characterized mesoionic chalcogenone supported metal derivatives. Furthermore, all zinc complexes were characterized by thermogravimetric analysis and UV-vis spectroscopy. The solid-state structures of all zinc complexes were determined by single-crystal X-ray diffraction. The catalytic activities of the zinc(ii) complexes in thioetherification reactions were investigated without scrubbing of oxygen. The scope of the catalytic reactions was explored with a wide range of thiophenols and aryl halides. The diaryl thioethers were obtained in very good yield under mild conditions. The present protocol furnishes a synthetic route for the C-S cross-coupling of thiophenols and aryl halides without scrubbing oxygen and moisture.
- Vaddamanu, Moulali,Prabusankar, Ganesan,Velappan, Kavitha
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p. 129 - 140
(2019/12/26)
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- CuMoO4 Bimetallic Nanoparticles, An Efficient Catalyst for Room Temperature C?S Cross-Coupling of Thiols and Haloarenes
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CuII catalyst is less efficient at room temperature for C?S cross-coupling. C?S cross-coupling by CuII catalyst at room temperature is not reported; however, doping of copper with molybdenum metal has been realized here to be more efficient for C?S cross-coupling in comparison to general CuII catalyst. The doped catalyst CuMoO4 nanoparticle is found to be more efficient than copper. The catalyst works under mild conditions without any ligand at room temperature and is recyclable and effective for a wide range of thiols and haloarenes (ArI, ArBr, ArF) from milligram to gram scale. The copper-based bimetallic catalyst is developed and recognized for C?S cross-coupling of haloarenes with alkyl and aryl thiols.
- Panigrahi, Reba,Sahu, Santosh Kumar,Behera, Pradyota Kumar,Panda, Subhalaxmi,Rout, Laxmidhar
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p. 620 - 624
(2019/12/27)
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- Method for synthesizing diarylthioether compound by using manganese oxide molecular sieve doped copper catalyst
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The invention relates to a synthesis method of a diarylthioether compound by catalyzing with heterogeneous manganese oxide octahedral molecular sieve doped copper (Cu-OMS-2). The chemical structural formula of the compound is shown in the description, whe
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Paragraph 0022
(2020/12/08)
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- An Iodide-Mediated Transition-Metal-Free Strategy towards Unsymmetrical Diaryl Sulfides via Arylhydrazines and Thiols
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A mild, scalable iodine-mediated oxidative cross-coupling reaction of arylhydrazines and thiols for construction of thioethers (sulfides) in the absence of any transition metals or photocatalysts is disclosed. A variety of unsymmetrical diaryl sulfides with broad substrate scope both on thiols and hydrazines were synthesized in high yields in water at room temperature. Furthermore, to demonstrate the utility of the protocol, the above C-S bond formation was applied in the synthesis of the key structure of vortioxetine as an antidepressant drug. The gram-scale outcome also added to the potential utility of this protocol.
- Asadpour, Mohammad,Azizzade, Meysam,Ghasemi, Mehran,Jafarpour, Farnaz,Rajai-Daryasarei, Saideh
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supporting information
p. 727 - 734
(2020/02/25)
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- Homoleptic and heteroleptic Zn(ii) selone catalysts for thioetherification of aryl halides without scrubbing oxygen
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Five new mononuclear tetra-coordinated zinc(ii) selones, [Zn(L1)2Cl2] (1), [Zn(L1)2Br2] (2), [{Zn(L2)4}{BF4}2] (3), [{Zn(L2)4}{ClO4}2] (4), and [Zn(L2)2Br2] (5), have been isolated from a one-pot reaction between the corresponding zinc(ii) salt and selone ligand, 1-methyl 3-naphthylmethylimidazoline-2-selone (L1) or 1-isopropyl 3-methylimidazoline-2-selone (L2). All these complexes were characterized by CHN analysis, FT-IR, NMR studies, and single-crystal X-ray crystallography techniques. The Zn(ii) center in 1-5 exhibits a distorted tetrahedral geometry. Besides, 1-5 were employed as catalysts in the thioetherification of aryl halides. The first zinc(ii) catalyst-mediated thioetherification of aryl halides without scrubbing oxygen was demonstrated. Catalysts 1-5 are highly active towards the cross-coupling reaction between aryl halides and thiophenols. The catalytic ability of 1-5 was explored in THF, toluene, and CH3CN solvents with different bases such as K2CO3, Cs2CO3, and NaOtBu. Interestingly, the zinc(ii) center attached to two selone ligands is much more catalytically active than that attached to four selone ligands.
- Vaddamanu, Moulali,Velappan, Kavitha,Prabusankar, Ganesan
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p. 3574 - 3583
(2020/03/17)
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- Anionic Bismuth(III) chloride cluster with diselenide countercations: Application in C-S cross coupling reactions
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The first weakly coordinating anion (WCA) with reactive p-block cation (rPBC) type of [(Bi4Cl16)4-{(LSeSeL)2+}2], L = 1,3-bis(2-benzhydryl-4,6-dimethylphenyl)-1H-imidazole-2(3H), ion pair is reported. The tetranuclear anionic bismuth(III) cluster shows a new type of ladder structure with two different types of Bi(III) coordination modes. In the solid state structure, the tetranuclear bismuth(III) cluster is sandwiched by two diselenide cations through hydrogen bonding interactions. Besides, this ion pair has been efficaciously employed as catalyst in C-S cross-coupling reactions under optimized reaction condition. This ion pair depicted a wide range of substrate scope with different thiols and aryl halides.
- Ganesan, Prabusankar,Mannem, Adinarayana,Muthukumaran, Nirmala
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supporting information
p. 29 - 35
(2019/02/08)
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- Copper(II)-faciliated synthesis of substituted thioethers and 5-substituted 1H-tetrazoles: Experimental and theoretical studies
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Benzoylhydrazine based Schiff base-ligated two new copper(II) complexes, [Cu(L1)2] (1) and [Cu(L2)2] (2) were synthesized by the reaction of Cu(CH3COO)2·H2O with respective Schiff base ligand 1-[(4-nitrophenyl)ethylidene] benzohydrazide (HL1) or 1-[(4-methoxyphenyl)ethylidene] benzohydrazide (HL2). Both complexes were isolated as greenish solid and fully characterized by elemental analysis, FT-IR, EPR, thermo-gravimetric (TG) analysis and Cyclic Voltammetry. The molecular structures of both complexes have also been determined by single crystal X-ray crystallography, which confirmed the coordination of Schiff base ligands through N, O donor atoms and distorted square planar geometry around the Cu(II) ion. Both complexes were found to be good homogeneous catalysts for the synthesis of a wide range of substituted thioethers and 5-substituted 1H-tetrazoles in 92% and 93% yield, respectively, at a low catalyst loading (0.5 mol%). The bond angles and distances, as discerned from the DFT calculations, commusurated with the experimental findings. The energy difference between the HOMO and the LUMO, calculated from DFT studies, was found to be 5.645 eV and 6.459 eV for complex 1 and complex 2, respectively. These results are in harmony with the observed higher catalytic activity of complex 1.
- Layek, Samaresh,Agrahari, Bhumika,Dey, Shuvankar,Ganguly, Rakesh,Pathak, Devendra D.
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p. 194 - 206
(2019/06/24)
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- Cerium catalyst promoted C-S cross-coupling: Synthesis of thioethers, dapsone and RN-18 precursors
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In this work, we present a novel, efficient and green methodology for the synthesis of thioethers by the C-S cross-coupling reaction with the assistance of [Ce(l-Pro)2]2Ox as a heterogeneous catalyst in good to excellent yields. A scale-up of the protocol was explored using an unpublished methodology for the synthesis of a dapsone-precursor, which proved to be very effective over a short time. The catalyst [Ce(l-Pro)2]2Ox was recovered and it was shown to be effective for five more reaction cycles.
- Tavares Junior, José M. Da C.,Da Silva, Caren D. G.,Dos Santos, Beatriz F.,Souza, Nicole S.,De Oliveira, Aline R.,Kupfer, Vicente L.,Rinaldi, Andrelson W.,Domingues, Nelson L. C.
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supporting information
p. 10103 - 10108
(2019/12/23)
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- CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides
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In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.
- Mohammadinezhad, Arezou,Akhlaghinia, Batool
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p. 15525 - 15538
(2019/10/19)
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- Aryldithiocarbamates as thiol alternatives in Cu-catalyzed C(aryl)-S coupling reactions using aryldiazonium tetrafluoroborate salts
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An efficient method for the synthesis of unsymmetrical diaryl sulfides has been developed by the C-S cross coupling of aryldithiocarbamates and aryldiazonium salts in the presence of CuI-2,2′-bipyridine and Zn. Aryldithiocarbamate compounds have been used here as thiol substitutes. The protocol shows wide substrate scope and good yields of the products.
- Dutta, Soumya,Saha, Amit
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p. 9360 - 9366
(2019/11/13)
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- C-S coupling with nitro group as leaving group via simple inorganic salt catalysis
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An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition-elimination mechanism.
- Xuan, Maojie,Lu, Chunlei,Lin, Bo-Lin
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supporting information
(2019/08/26)
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- Transition-Metal-Free Aryl-Heteroatom Bond Formation via C-S Bond Cleavage
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Aryl-heteroatom bonds (C-Het) are almost ubiquitously present in chemical molecules. However, methods for diverse C-Het bond formations from a simple substrate are limited. Herein, we report a convenient and efficient C-S bond transformation of aryl sulfoniums to various C-Het bonds (C-O, C-S, C-Sn, C-Si, C-Se) in the absence of any transition-metal catalyst. These reactions proceeded in mild conditions with a wide substrate scope.
- Zhao, Jian-Nan,Kayumov, Muzaffar,Wang, Dong-Yu,Zhang, Ao
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p. 7303 - 7306
(2019/10/02)
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- Palladium-Catalyzed Oxidative Cross-Coupling of Arylhydrazines and Arenethiols with Molecular Oxygen as the Sole Oxidant
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A highly efficient palladium-catalyzed oxidative cross-coupling of arylhydrazines and arenethiols with molecular oxygen as the sole oxidant to afford unsymmetrical diaryl sulfides has been developed. The only byproducts are nitrogen and water. A broad range of functional groups, even the reactive iodides, are tolerated and thus offer the opportunity for further functionalization.
- Wang, Changliu,Zhang, Zhenming,Tu, Yongliang,Li, Ying,Wu, Jiale,Zhao, Junfeng
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p. 2389 - 2394
(2018/02/23)
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- Transition-Metal-Free and Oxidant-Free Cross-Coupling of Arylhydrazines with Disulfides: Base-Promoted Synthesis of Unsymmetrical Aryl Sulfides
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A novel synthesis of unsymmetrical aryl sulfides, which requires no transition metal catalyst and no oxidant, was developed. This base-promoted cross-coupling reaction proceeded using arylhydrazines and 1 equiv amount of disulfides under inert gas conditions to afford the unsymmetrical aryl sulfides in good yields.
- Taniguchi, Toshihide,Naka, Takuya,Imoto, Mitsutaka,Takeda, Motonori,Nakai, Takeo,Mihara, Masatoshi,Mizuno, Takumi,Nomoto, Akihiro,Ogawa, Akiya
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p. 6647 - 6655
(2017/07/15)
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- The copper-nicotinamide complex: Sustainable applications in coupling and cycloaddition reactions
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The crystalline copper(ii)-nicotinamide complex, synthesized via simple mixing of copper chloride and nicotinamide solution at room temperature, catalyzes the C-S, C-N bond forming and cycloaddition reactions under a variety of sustainable reaction conditions.
- Baig, R.B. Nasir,Vaddula, Buchi Reddy,Nadagouda, Mallikarjuna N.,Varma, Rajender S.
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supporting information
p. 1243 - 1248
(2015/03/04)
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- Tridentate hydroxy-functionalised MCM-41-immobilised copper(I) complex as an efficient and recyclable catalyst for coupling of aryl iodides with thiols
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The C-S coupling reaction of aryl iodides with thiols was achieved at 110 °C in DMF/dioxane (V/V, 1:9) in the presence of a tridentate hydroxy-functionalised MCM-41-immobilised copper(I) complex [MCM-41-3OH-CuI] with Cs2CO3 as base to afford a variety of diaryl sulfides in good to excellent yields. The MCM-41-3OH-CuI catalyst can be easily recovered by a simple filtration and reused for at least six times without significant loss of activity.
- Yao, Fang,Zhang, Rongli,Wu, Yichao,Cai, Mingzhong
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p. 612 - 616
(2015/11/27)
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- Iridium and phosphine promoted C-F bond activation: The C-S cross-coupling of aryl fluorides with diaryl disulfides to synthesize thioethers
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Carbon-fluorine bond is the strongest known single bond to carbon and proved very difficult to cleave. An iridium and phosphine promoted C-F bond activation was developed, for the first time achieving the C-S cross-coupling reaction of disulfides with aryl fluorides using iridium complex. The corresponding monoarylthiolation products were obtained at moderate to good yields. Thus, it represents a new method for the synthesis of aryl sulfides through C-F bond activation.
- Li, Liang,Miao, Hongyan,Ding, Yuqiang
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supporting information
p. 6405 - 6408
(2015/11/16)
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- Ascorbic Acid Promoted Metal-Free Synthesis of Aryl Sulfides with Anilines Nitrosated in Situ by tert -Butyl Nitrite
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A mild, metal-free synthesis of aryl sulfides has been disclosed. Aryl diazonium ion was generated by the in situ nitrosation of aniline, and it was reduced by ascorbic acid (vitamin C) to form aryl radical, which underwent a thiolation with disulfide to yield aryl sulfide. The reaction proceeded smoothly without heating or irradiation. This strategy was also expanded to the synthesis of aryl selenides.
- Bu, Mei-Jie,Lu, Guo-Ping,Cai, Chun
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supporting information
p. 1841 - 1846
(2015/08/06)
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- Oxo-rhenium(V) complexes containing heterocyclic ligands as catalysts for the reduction of sulfoxides
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This work reports the catalytic activity of a large variety of oxo-rhenium(V) complexes (1 mol-%) containing the ligands 2-(2-hydroxy-5- methylphenyl)benzotriazole (Hhmpbta), 2-(2-hydroxyphenyl)benzothiazole (Hhpbt), 2-(2-hydroxyphenyl)benzoxazole (Hhpbo), and 2-(2-hydroxyphenyl)-1H-benzimidazole (Hhpbi) in the deoxygenation of sulfoxides with silanes or boranes as the reducing agents. In general, all of the complexes are excellent catalysts, although the PhSiH3/[ReOBr2(hmpbta)(PPh3)] and pinacolborane/[ReOBr2(hmpbta)(PPh3)] systems are the most efficient for the reduction of aromatic and aliphatic sulfoxides and tolerate different functional groups. Copyright
- Sousa, Sara C. A.,Bernardo, Joana R.,Wolff, Mariusz,Machura, Barbara,Fernandes, Ana C.
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p. 1855 - 1859
(2014/04/03)
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- Oxo-Rhenium(V) Complexes Containing Heterocyclic Ligands as Catalysts for the Reduction of Sulfoxides
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This work reports the catalytic activity of a large variety of oxo-rhenium(V) complexes (1 mol-%) containing the ligands 2-(2-hydroxy-5-methylphenyl)benzotriazole (Hhmpbta), 2-(2-hydroxyphenyl)benzothiazole (Hhpbt), 2-(2-hydroxyphenyl)benzoxazole (Hhpbo), and 2-(2-hydroxyphenyl)-1H-benzimidazole (Hhpbi) in the deoxygenation of sulfoxides with silanes or boranes as the reducing agents. In general, all of the complexes are excellent catalysts, although the PhSiH3/[ReOBr2(hmpbta)(PPh3)] and pinacolborane/[ReOBr2(hmpbta)(PPh3)] systems are the most efficient for the reduction of aromatic and aliphatic sulfoxides and tolerate different functional groups.
- Sousa, Sara C. A.,Bernardo, Joana R.,Wolff, Mariusz,Machura, Barbara,Fernandes, Ana C.
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supporting information
p. 1855 - 1859
(2015/10/05)
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- Organic synthesis via magnetic attraction: Benign and sustainable protocols using magnetic nanoferrites
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Magnetic nano-catalysts have been prepared using simple modification of iron ferrites. The nm size range of these particles facilitates the catalysis process, as an increased surface area is available for the reaction; the easy separation of the catalysts by an external magnet and their recovery and reuse are additional beneficial attributes. Glutathione bearing nano-ferrites have been used as organocatalysts for the Paal-Knorr reaction and homocoupling of boronic acids. Nanoferrites, post-synthetically modified by ligands, were used to immobilize nanometals (Cu, Pd, Ru, etc.) which enabled the development of efficient, sustainable and green procedures for azide-alkynes-cycloaddition (AAC) reactions, C-S coupling, O-allylation of phenol, Heck-type reactions and hydration of nitriles.
- Nasir Baig,Varma, Rajender S.
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p. 398 - 417
(2013/03/14)
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- KF/clinoptilolite: An efficient promoter for the synthesis of thioethers
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Potassium fluoride impregnated on natural zeolite as a new solid base system effectively catalyzes the coupling of thiophenols with electron-deficient fluoro-, chloro- and bromo-arenes in DMSO. This versatile and efficient solid base has been demonstrated to afford the corresponding desired products in good to excellent yields. This procedure provides a convenient, efficient and practical method for the preparation of diaryl thioethers.
- Salmanpour, Sadegh,Khalilzadeh, Mohammad A.,Hosseini, Abolfazl
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p. 339 - 344
(2013/07/28)
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- Ligand-free solid supported palladium(0) nano/microparticles promoted C-O, C-S, and C-N cross coupling reaction
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Ligand-free solid-supported nano and microparticles of Pd(0) (SS-Pd) were used as a heterogeneous catalyst in carbon-heteroatom bond formation reactions. Nitro substituted aryl halides reacted with oxygen, sulfur, and nitrogen nucleophiles to afford the corresponding products in good yields. A one-pot sequential cross coupling and nitro-reduction was also performed using the same SS-Pd catalyst to access amine substituted carbon-heteroatomic molecules. In addition, SS-Pd could be recycled up to seven runs without a significant loss of catalytic activity.
- Bandna,Guha, Nitul Ranjan,Shil, Arun K.,Sharma, Dharminder,Das, Pralay
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supporting information
p. 5318 - 5322
(2012/10/30)
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- A highly active and magnetically retrievable nanoferrite-DOPA-copper catalyst for the coupling of thiophenols with aryl halides
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Diaryl sulfides were synthesized using a magnetically recoverable heterogeneous Cu catalyst via one-pot multi component reaction using MW irradiation; the use of isopropanol as a benign reaction medium, easy recovery of the catalyst using an external magnet, efficient recycling, and the high stability of the catalyst render the protocol economic and sustainable. This journal is The Royal Society of Chemistry 2012.
- Baig, R. B. Nasir,Varma, Rajender S.
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supporting information; experimental part
p. 2582 - 2584
(2012/03/26)
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- Highly efficient rhenium-catalyzed deoxygenation of sulfoxides without adding any reducing agent
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This work reports a novel method for the deoxygenation of aromatic and aliphatic sulfoxides catalyzed by oxo-rhenium complexes without adding any reducing agent. The oxo-rhenium complex ReOCl3(PPh3) 2 proved to be very efficient for the deoxygenation of several sulfoxides with tolerance of different functional groups.
- Sousa, Sara C.A.,Bernardo, Joana R.,Rom?o, Carlos C.,Fernandes, Ana C.
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experimental part
p. 8194 - 8197
(2012/09/22)
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- Microwave-promoted TBAF-catalyzed SNAr reaction of aryl fluorides and ArSTMS: An efficient synthesis of unsymmetrical diaryl thioethers
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Microwave irradiation was found to promote tetrabutylammonium fluoride catalyzed nucleophilic aromatic substitution of aryl fluorides and arylthiotrimethylsilanes, affording high yields of unsymmetrical diaryl thioethers efficiently under mild, transition-metal- and base-free conditions. Microwave showed unusual improvement on the reaction in not only the conditions and reaction rate, but also in selectivity and substrate scope. Georg Thieme Verlag Stuttgart - New York.
- Liu, Chuanzhi,Zang, Xufeng,Yu, Baohua,Yu, Xiaochun,Xu, Qing
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supporting information; experimental part
p. 1143 - 1148
(2011/07/09)
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- Microwave-assisted cross-coupling for the construction of diaryl sulfides
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The construction of diaryl sulfides through the cross-coupling of aryl iodides and thiols in microwave heating is described. By using this method, a variety of diaryl sulfides can be prepared in a mild condition and in high yields. Deactivated 4-nitrothiophenol was effective to afford the product in 94% yield. Sterically hindered ortho-substituted aryl iodides or thiophenols provided diaryl sulfides effectively by this microwave-assisted coupling reaction.
- Tan, Chen-Ming,Chen, Grace Shiahuy,Chena, Chien-Shu,Chern, Ji-Wang
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experimental part
p. 94 - 100
(2011/11/06)
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- A highly efficient method for the copper-catalyzed selective synthesis of diaryl chalcogenides from easily available chalcogen sources
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An efficient protocol for copper-catalyzed C-S or C-Se bond formation between aryl iodides and easily available chalcogen sources leading to diaryl chalcogenides is reported. A variety of symmetrical diaryl sulfides and diaryl selenides were synthesized in good to excellent yields. Unsymmetrical diaryl sulfides were also obtained in moderate yields from two different aryl iodides by a one-pot tandem process. This strategy was further successfully utilized for the synthesis of 2-phenylbenzo[b]thiophene and of [1]benzothieno[3,2-b] benzothiophene. A new Cu-catalyzed one-pot approach for the selective synthesis of symmetrical diaryl chalcogenides and unsymmetrical diarylsulfides with use of Na2S or Se as chalcogen sources has been developed. Copyright
- Li, Yaming,Nie, Caiping,Wang, Huifeng,Li, Xiaoying,Verpoort, Francis,Duan, Chunying
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p. 7331 - 7338
(2012/01/06)
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- A reusable FeCl3·6H2O/cationic 2,2′-bipyridyl catalytic system for the coupling of aryl iodides with thiols in water under aerobic conditions
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In this study, an FeCl3·6H2O/cationic 2,2′-bipyridyl system was employed as a catalyst in the coupling of aryl iodides with thiols to form an aryl-sulfur bond in refluxed water under aerobic conditions. The residual aqueous solution after extraction could be reused for several cycles without a significant decrease in activity.
- Wu, Wei-Yi,Wang, Jui-Chan,Tsai, Fu-Yu
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experimental part
p. 326 - 329
(2010/04/22)
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- Efficient ligand-free nickel-catalyzed C-S cross-coupling of thiols with aryl iodides
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NiCl2·6H2O efficiently catalyzes the C-S bond formation by the cross-coupling of aryl iodides with thiols in tetrabutylammonium bromide (TBAB) in excellent yield. The reaction functions in air and the NiLn-TBAB can be recovered and recycled without the loss of activity.
- Jammi, Suribabu,Barua, Priyanka,Rout, Laxmidhar,Saha, Prasenjit,Punniyamurthy, Tharmalingam
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p. 1484 - 1487
(2008/09/18)
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- Ligand-free C-S bond formation catalyzed by copper(I) oxide
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An efficient ligand-free Cu2O-catalyzed C-S bond-formation reaction was developed. A large number of diaryl sulfides and alkylaryl sulfides could be rapidly assembled using this new reaction protocol. Georg Thieme Verlag Stuttgart.
- Xu, Hua-Jian,Zhao, Xiao-Yang,Fu, Yao,Feng, Yi-Si
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experimental part
p. 3063 - 3067
(2009/07/04)
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- Copper-catalyzed Ullmann coupling under ligand- and additive-free conditions. Part 2: S-Arylation of thiols with aryl iodides
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S-Arylation of a wide variety of substituted aryl and aliphatic thiols with aryl halides catalyzed by copper iodide under mild ligand- and additive-free conditions (nBu4NBr, PhMe, NaOH, reflux, 22 h) is accomplished in good to excellent product yields (up to 96%).
- Buranaprasertsuk, Pongchart,Chang, Joyce Wei Wei,Chavasiri, Warinthorn,Chan, Philip Wai Hong
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p. 2023 - 2025
(2008/09/19)
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- GLYT2 MODULATORS
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α-, β-, and γ-amino acid derivatives of formula I are disclosed as selective GlyT2 inhibitors for the treatment of central nervous system (CNS) conditions such as muscle spasticity, tinnitus, epilepsy and neuropathic pain. Formula I
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Page/Page column 113
(2010/02/11)
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- Discovery and SAR development of 2-(phenylamino) imidazolines as postacyclin receptor antagonists
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On the basis of screening hits (1a,b), a series of selective, high affinity prostacyclin receptor antagonists was developed. The optimized lead compound 25d [(4,5-dihydro-1H-imidazol-2-yl)-[4-(4-isopropoxybenzyl)phenyl] amine] had analgesic activity in the rat.
- Clark, Robin D.,Jahangir, Alam,Severance, Daniel,Salazar, Rick,Chang, Thomas,Chang, David,Jett, Mary Frances,Smith, Steven,Bley, Keith
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p. 1053 - 1056
(2007/10/03)
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- Phosphazene bases for the preparation of biaryl thioethers from aryl iodides and arenethiols
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In the presence of phosphazene P2-Et base as well as 1,8- diazabicyclo[5.4.0]undec-7-ene (DBU) the coupling of aryl iodides with arenethiois only requires catalytic amounts of CuBr. Under these conditions the reaction can be performed in refluxing toluene to give biaryl thioethers in excellent yields. (C) 2000 Elsevier Science Ltd.
- Palomo, Claudio,Oiarbide, Mikel,López, Rosa,Gómez-Bengoa, Enrique
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p. 1283 - 1286
(2007/10/03)
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- KINETIC RELATIONSHIPS OF THE REACTION OF 4-NITROHALOGENOBENZENES WITH SUBSTITUTED POTASSIUM THIOPHENOLATES
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The kinetic relationships governing the substitution of the halogen atom in 4-nitrohalogenobenzenes by a phenylthio group were studied, and the kinetic and thermodynamic parameters of the process were determined.A quantitative assessment of the sensitivity of the reaction to the effect of the substituent in the reagent and the leaving group of the substrate is given.It is concluded that a two-stage SNAr "addition-elimination" mechanism is realized.
- Nikiforov, A. V.,Alov, E. M.,Moskvichev, Yu. A.,Mironov, G. S.,Kryukova, G. G.,Smirnova, T. M.
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p. 933 - 936
(2007/10/02)
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- CONVENIENT ONE-POT SYNTHESIS OF ARENESULFINAMIDES: REACTIONS OF 4-NITROPHENYL SUBSTITUTED PHENYL SULFOXIDES WITH ELEMENTAL SULFUR IN LIQUID AMMONIA
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Various arenesulfinamides were synthesized in good yields by one-pot reactions of 4-nitrophenyl-substituted phenyl sulfoxides with elemental sulfur in liquid ammonia.The arenesulfinamides were further reduced with elemental sulfur in liquid ammonia to give corresponding disulfides.
- Sato, Ryu,Chiba, Shuji,Takikawa, Yuji,Takizawa, Saburo,Saito, Minoru
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p. 535 - 538
(2007/10/02)
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- Magenta-masked color azopyrazolinone couplers
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Orange colored magenta color couplers of the general formula STR1 are provided, in which R is optionally substituted alkyl, aralkyl, aryl or a heterocyclic group, X is optionally substituted aryl, Y is optionally substituted acyl-amino, aroyl amino or aryl amino and Z represents further optional substituents of the phenyl ring. Preferably Y also contains a ballasting group, which is a long claim alkyl group having 10 to 24 carbon atoms in the chain.
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