- Magnetically recoverable ferromagnetic 3D hierarchical core-shell Fe3O4@NiO/Co3O4 microspheres as an efficient and ligand-free catalyst for C–S bond formation in poly (ethylene glycol)
-
A simple and efficient protocol for the synthesis of diaryl thioethers from the reaction of thiourea with a wide variety of aryl halides, including aryl iodides, aryl bromides and aryl chlorides in the presence of 3D hierarchical core-shell Fe3O4@NiO/Co3O4 microspheres has been described. This reaction enables the one-pot synthesis of diaryl thioethers in good to high yields using a non-toxic and magnetically separable catalyst in PEG-400 as an eco-friendly, safe, inexpensive and thermally stable solvent. Magnetic separation and reusability of catalyst for eight times without any significant loss of activity, the use of a commercially available, eco-friendly, cheap and chemically stable sulfur transfer agent and solvent, operational simplicity, environmentally benign, easier work-up procedure and cost efficiency make this method a promising candidate for potential applications in some organic reactions. The catalytic activity of Fe3O4@NiO/Co3O4 as a novel and inexpensive catalyst was investigated in the C-S cross coupling reaction.
- Vatandoust Namanloo, Ahad,Akhlaghinia, Batool,Mohammadinezhad, Arezou
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p. 446 - 461
(2020/05/13)
-
- Copper-catalyzed diastereoselective hydrothioetherification of oxa(aza)benzonorbornadienes
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A novel copper-catalyzed hydrothioetherification of oxa(aza)bicyclic alkenes with potassium thioacetate and aryl or alkyl iodides to synthesize unsymmetrical thioethers has been developed. Notably, the reaction with complete diastereoselectivity went through a syn-selective addition process to give exo-adducts. In addition, this protocol exhibited high efficiency and good functional group tolerance to afford the target thioethers in moderate to good yields. Based on the results of mechanistic investigations, a plausible mechanism was proposed.
- Chen, Donghan,Chen, Shuqi,Lin, Qifu,Tan, Yun,Yang, Dingqiao,Yang, Wen,Yao, Yongqi
-
p. 3575 - 3584
(2020/06/10)
-
- CuI anchored onto mesoporous SBA-16 functionalized by aminated 3-glycidyloxypropyltrimethoxysilane with thiosemicarbazide (SBA-16/GPTMS-TSC-CuI): A heterogeneous mesostructured catalyst for: S -arylation reaction under solvent-free conditions
-
Herein, we report the novel synthesis of CuI anchored onto a cage-like mesoporous material (SBA-16), which was successfully functionalized by aminated 3-glycidyloxypropyltrimethoxysilane with thiosemicarbazide (SBA-16/GPTMS-TSC-CuI) into an efficient and highly recyclable heterogeneous catalyst. The as-synthesized mesostructured catalyst (SBA-16/GPTMS-TSC-CuI) was comprehensively characterized by different techniques, namely, FT-IR, FIR, SAXRD, XRD, XPS, BET, TEM, FE-SEM, EDX, EDX mapping, TGA, ICP-OES, and CHNS analyses. SBA-16 with a unique "super-cage" structure efficiently controlled the formation of dispersed organic and metal species in the mesoporous channels. These confined nanoparticles with a narrow particle size distribution (3-7 nm) exhibited excellent catalytic activity in the S-arylation reaction without necessitating the use of toxic solvents and/or expensive metal catalysts. Interestingly, the mesoporous catalyst was extremely stable under the reaction conditions and could be easily separated by a simple filtration process and reused for at least seven recycle runs (without any appreciable loss in catalytic activity). Due to the inimitable structure of the abovementioned mesostructured catalyst, the C-S coupling products of aryl halides with S8/thiourea under solvent-free conditions were obtained in good to excellent yields in remarkably reduced reaction times in comparison to those reported in earlier studies.
- Ghodsinia, Sara S.E.,Akhlaghinia, Batool
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p. 3029 - 3049
(2019/06/17)
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- NiFe2O4 as a magnetically recoverable nanocatalyst for odourless C–S bond formation via the cleavage of C–O bond in the presence of S8 under mild and green conditions
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We present green methodologies for one-pot and odourless syntheses of unsymmetric and symmetric diaryl sulfides via C─O bond activation using NiFe2O4 magnetic nanoparticles as a reusable heterogeneous nanocatalyst. The synthesis of unsymmetric sulfides is performed using the cross-coupling reaction of phenolic esters such as acetates, triflates and tosylates with arylboronic acid/S8 or triphenyltin chloride/S8 as thiolating agents in the presence of base and NiFe2O4 magnetic nanoparticles as a catalyst in poly(ethylene glycol) as solvent at 60–85°C. Also, the synthesis of symmetric diaryl sulfides from phenolic compounds using S8 as the sulfur source and NiFe2O4 as catalyst in dimethylformamide at 120°C is described. Using these protocols, the syntheses of various unsymmetric and symmetric sulfides become easier than using the available protocols due to the use of a magnetically reusable bimetallic nanocatalyst and avoiding the use of thiols and aryl halides.
- Atashkar, Bahareh,Rostami, Amin,Rostami, Abed,Zolfigol, Mohammad Ali
-
-
- Proton-Activated “Off–On” Room-Temperature Phosphorescence from Purely Organic Thioethers
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Room-temperature phosphorescence (RTP)-based sensors have distinctive advantages over the fluorescence counterparts, such as larger Stokes shifts and longer lifetimes. Unfortunately, almost all RTP sensors are operated on quenching-based mechanisms given the sensitive nature of the emissive triplet state. Here we report a type of thioether RTP molecules that shows RTP “turn-on” when volatile acid vapors such as HCl are in contact. To elucidate the underlying mechanism, model thioethers containing different donor/acceptor combinations are investigated via fluorescence spectroscopy and theoretical calculations aided by molecular coordinates obtained from single-crystal X-ray diffraction. It is revealed that a charge-transfer character in the phosphorescence state is crucial. The “turn-on” design concept may significantly broaden the sensing application scope for organic RTP molecules.
- Huang, Linkun,Chen, Biao,Zhang, Xuepeng,Trindle, Carl O.,Liao, Fan,Wang, Yucai,Miao, Hui,Luo, Yi,Zhang, Guoqing
-
supporting information
p. 16046 - 16050
(2018/11/23)
-
- Copper-Catalyzed Production of Diaryl Sulfides Using Aryl Iodides and a Disilathiane
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A disilathiane was found to be a novel S1 source for the copper-catalyzed synthesis of diaryl sulfides using aryl iodides. The reaction of iodoarenes and hexamethyldisilathiane, (Me 3 Si) 2 S, in the presence of a catalytic amount of CuI/1,10-phenanthroline provided various types of diaryl sulfides in good yields.
- Ogiwara, Yohei,Maeda, Hiromu,Sakai, Norio
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supporting information
p. 655 - 657
(2017/11/29)
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- 4-(Phenoxy) and 4-(benzyloxy)benzamides as potent and selective inhibitors of mono-ADP-ribosyltransferase PARP10/ARTD10
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Human Diphtheria toxin-like ADP-ribosyltranferases (ARTD) 10 is an enzyme carrying out mono-ADP-ribosylation of a range of cellular proteins and affecting their activities. It shuttles between cytoplasm and nucleus and influences signaling events in both compartments, such as nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) signaling and S phase DNA repair. Furthermore, overexpression of ARTD10 induces cell death. We recently reported on the discovery of a hit compound, OUL35 (compound 1), with 330 nM potency and remarkable selectivity towards ARTD10 over other enzymes in the human protein family. Here we aimed at establishing a structure-activity relationship of the OUL35 scaffold, by evaluating an array of 4-phenoxybenzamide derivatives. By exploring modifications on the linker between the aromatic rings, we identified also a 4-(benzyloxy)benzamide derivative, compound 32, which is potent (IC50 = 230 nM) and selective, and like OUL35 was able to rescue HeLa cells from ARTD10-induced cell death. Evaluation of an enlarged series of derivatives produced detailed knowledge on the structural requirements for ARTD10 inhibition and allowed the discovery of further tool compounds with submicromolar cellular potency that will help in understanding the roles of ARTD10 in biological systems.
- Murthy, Sudarshan,Desantis, Jenny,Verheugd, Patricia,Maksimainen, Mirko M.,Venkannagari, Harikanth,Massari, Serena,Ashok, Yashwanth,Obaji, Ezeogo,Nkizinkinko, Yves,Lüscher, Bernhard,Tabarrini, Oriana,Lehti?, Lari
-
-
- Copper-Catalyzed C-S Bond Formation via the Cleavage of C-O Bonds in the Presence of S8 as the Sulfur Source
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Useful and applicable methods for one-pot and odorless synthesis of unsymmetrical and symmetrical diaryl sulfides via C-O bond activation are presented. First, a new efficient procedure for the synthesis of unsymmetrical sulfides using the cross-coupling reaction of phenolic esters such as acetates, tosylates, and triflates and with arylboronic acid or triphenyltin chloride as the coupling partners is reported. Depending on the reaction, S 8 /KF or S 8 /NaO t -Bu system is found to be an effective source of sulfur in the presence of copper salts and in poly(ethylene glycol) as a green solvent. Then, the synthesis of symmetrical diaryl sulfides from phenolic compounds by using S 8 as the sulfur source and NaO t -Bu in anhydrous DMF at 120 °C under N 2 is described. By these protocols, the synthesis of a variety of unsymmetrical and symmetrical sulfides become easier than the available protocols in which thiols and aryl halides are directly used for the preparation of the sulfides.
- Rostami, Abed,Rostami, Amin,Ghaderi, Arash,Gholinejad, Mohammad,Gheisarzadeh, Sajedeh
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p. 5025 - 5038
(2017/10/06)
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- Anchoring of Cu(II)–vanillin Schiff base complex on MCM-41: A highly efficient and recyclable catalyst for synthesis of sulfides and 5-substituted 1H–tetrazoles and oxidation of sulfides to sulfoxides
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A copper(II)–vanillin complex was immobilized onto MCM-41 nanostructure and was used as an inexpensive, non-toxic and heterogeneous catalyst in the synthesis of symmetric aryl sulfides by the cross-coupling of aromatic halides with S8 as an effective sulfur source, in the oxidation of sulfides to sulfoxides using 30% H2O2 as a green oxidant and in the synthesis of 5-substituted 1H–tetrazoles from a smooth (3?+?2) cycloaddition of organic nitriles with sodium azide (NaN3). The products were obtained in good to excellent yields. This catalyst could be reused several times without loss of activity. Characterization of the catalyst was performed using Fourier transform infrared, energy-dispersive X-ray and atomic absorption spectroscopies, X-ray diffraction, thermogravimetric analysis, and scanning and transmission electron microscopies.
- Khanmoradi, Maryam,Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash
-
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- Ligand-free copper-catalysed direct synthesis of diaryl sulfides and diaryl disulfides in wet poly(ethylene glycol)
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An improved protocol has been developed for the one-pot CuI-catalysed preparation of symmetric diaryl sulfides from their available aryl halides in the presence of thiourea as sulfur transfer agent and in the absence of both ligand and organic solvent. This catalytic system was also used for the high-yielding preparation of diaryl disulfides in the presence of C2Cl6 as oxidant.
- Nowrouzi, Najmeh,Abbasi, Mohammad,Latifi, Hadis
-
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- Efficient Cu-catalyzed one-pot odorless synthesis of sulfides from triphenyltin chloride, aryl halides and S8 in PEG
-
A novel method for the Cu(OAc)2 catalyzed synthesis of unsymmetrical sulfides from triphenyltin chloride and aryl halides using S8 as the sulfur source in PEG200 at 60-80°C is reported. Triphenyltin chloride is capable of delivering all of its phenyl groups to the product. Also, the copper catalyzed synthesis of symmetrical diaryl sulfides from aryl halides using S8 is described.
- Rostami, Abed,Rostami, Amin,Iranpoor, Nasser,Zolfigol, Mohammad Ali
-
supporting information
p. 192 - 195
(2015/12/30)
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- Microwave-assisted, metal- and solvent-free synthesis of diaryl thioethers from aryl halides and carbon disulfide in the presence of [DBUH]+[OAc]-
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A microwave-assisted direct coupling between aryl halides and carbon disulfide in ionic liquid [DBUH]+[OAc]- (DBU = 1,8-diazabicyclo-[5.4.0] undec-7-ene) has been developed. The reactions are very efficient, affording the corresponding diaryl thioethers in moderate to high yields. Aryl chlorides could also be reacted with carbon disulfide using this protocol. Moreover, [DBUH]+[OAc]- could be easily recovered and reused for several runs.
- Zhou, Yongsheng
-
p. 305 - 307
(2016/07/06)
-
- Metal-free catalytic synthesis of diaryl thioethers under mild conditions
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A novel method to synthesize diaryl thioethers from aryl halides and carbon disulfide catalyzed by the 1,8-diazabicyclo[5,4,0]undec-7-enium acetate [DBUH][OAc] ionic liquid (IL) under solvent-free conditions has been developed. This metal-free catalytic system displayed high efficiency for coupling aryl halides with CS2 to deliver thioethers. Compared to the conventional methods, no metal catalyst was needed, instead of which the DBU-based ILs played the catalyst and solvent roles simultaneously. Some reactions were carried out under mild conditions (55 °C, 0.5 h), giving moderate to high yields. Moreover, compared with the rare reports, the reaction of the aryl chlorides and fluorides with CS2 could smoothly react in this catalytic system. The products were easily separated from the ILs which could be reused at least three times. The present method provides an efficient and environment-friendly catalytic approach to synthesize diaryl thioethers.
- Cao, Xian-Ting,Zhang, Peng-Fei,Zheng, Hui
-
supporting information
p. 6762 - 6767
(2016/08/10)
-
- Fe-Cu catalyzed synthesis of symmetrical and unsymmetrical diaryl thioethers using 1,3-benzoxazole-2-thiol as a sulfur surrogate
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An efficient Fe-Cu catalyzed approach is herein developed using 1,3-benzoxazole-2-thiol as a thiol surrogate for the synthesis of symmetrical and unsymmetrical diaryl thioethers. This method provides an odorless and inexpensive strategy which can be applied to various aryl and nitrogen containing aryl halides in moderate to excellent yields up to 90%.
- Tber,Hiebel,El Hakmaoui,Akssira,Guillaumet,Berteina-Raboin
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p. 72030 - 72036
(2016/08/09)
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- Thiol-free route to diaryl sulfides by Cu catalyzed coupling of sodium thiosulfate with aryl halides
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A method for the synthesis of diaryl sulfides from aryl halides in polyethylene glycol was reported. Inodorous Na2S2O3·5H2O, which is readily available as a stable salt, is an effective source of sulfur in the presence of CuI as catalyst.
- Nowrouzi, Najmeh,Abbasi, Mohammad,Latifi, Hadis
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p. 1550 - 1554
(2016/10/04)
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- Highly efficient and reusable polystyrene-supported copper(II) catalytic system for S-arylation of potassium thiocyanate by aryl halides in water
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An inexpensive, efficient and environmentally friendly copper(II) catalyst supported on polystyrene was successfully synthesized and used as a heterogeneous catalyst for S-arylation of potassium thiocyanate by aryl halides. Also this catalyst could be recovered and reused several times without any noticeable decrease in its catalytic activity. Copyright
- Hajipour, Abdol R.,Jajarmi, Saeideh
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p. 566 - 570
(2016/07/16)
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- Selective synthesis of organic sulfides or disulfides by solvent exchange from aryl halides and KSCN catalyzed by NiCl2·6H2O
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A method for selective synthesis of symmetric sulfides or disulfides from the reaction of aryl halides with KSCN by solvent exchange is introduced. Aryl halides were selectively converted to the symmetric disulfides or sulfides in high yields when they are treated with KSCN in the presence of NiCl2·6H2O and DMAP at 140?°C in DMF or poly ethylene glycol (PEG-200) respectively.
- Abbasi, Mohammad,Nowrouzi, Najmeh,Latifi, Hadis
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p. 112 - 117
(2016/09/07)
-
- Stabilized naked Sub-nanometric Cu clusters within a polymeric film catalyze C-N, C-C, C-O, C-S, and C-P bond-forming reactions
-
Sub-nanometric Cu clusters formed by endogenous reduction of Cu salts and Cu nanoparticles are active and selective catalysts for C-N, C-C, C-O, C-S, and C-P bond-forming reactions. Sub-nanometric Cu clusters have also been generated within a polymeric film and stored with full stability for months. In this way, they are ready to be used on demand and maintain high activity (TONs up to 104) and selectivity for the above reactions. A potential mechanism for the formation of the sub-nanometric clusters and their electronic nature is presented.
- Oliver-Messeguer, Judit,Liu, Lichen,García-García, Saray,Canós-Giménez, Claudia,Domínguez, Irene,Gavara, Rafael,Doménech-Carbó, Antonio,Concepción, Patricia,Leyva-Pérez, Antonio,Corma, Avelino
-
supporting information
p. 3894 - 3900
(2015/04/14)
-
- Sonication effect on the reaction of 4-bromo-1-methylbenzene with sodium sulfide in liquid-liquid multi-site phase-transfer catalysis condition - Kinetic study
-
The synthesis of di-p-tolylsulfane from the reaction of 4-bromo-1-methylbenzene (BMB) with sodium sulfide was carried out using a multi-site phase-transfer catalyst (MPTC) viz., 1,4-dihexyl-1,4-diazoniabicyclo[2.2.2]octanium dibromide and ultrasonic irradiation in a liquid-liquid reaction condition. The overall reaction rate is greatly enhanced when catalyzed by multi-site phase-transfer catalyst (MPTC) combined with sonication (40 kHz, 300 W) in a batch reactor than catalyzed by MPTC without sonication. Effects on the reaction due to various operating conditions, such as agitation speed, different ultrasound frequencies, different phase-transfer catalysts, different organic solvents, the amount of MPTC, temperature, amount of sodium sulfide, effect of sodium hydroxide, volume of n-hexane and the concentration of 4-bromo-1-methylbenzene. The reaction obeys a pseudo first-order rate law and a suitable mechanism was proposed based on the experimental observation.
- Abimannan, Pachaiyappan,Selvaraj, Varathan,Rajendran, Venugopal
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p. 156 - 164
(2015/02/19)
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- Synthesis of diaryl thioethers from aryl halides and potassium thiocyanate
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An efficient palladium catalyst was synthesized using nicotine, benzyl chloride and palladium chloride. The structure of this catalyst was characterized and it was then used for the synthesis of diaryl sufides. A variety of diaryl thioethers were synthesized under relatively mild reaction conditions. This protocol avoids foul-smelling thiols via cross-coupling of aryl halides with potassium thiocyanate and all substrates give the corresponding products in good to excellent yields in the presence of low amounts of the catalyst.
- Hajipour, Abdol R.,Pourkaveh, Raheleh,Karimi, Hirbod
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p. 879 - 883
(2015/02/05)
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- A simple, efficient and recyclable catalytic system for carbon-sulfur coupling of aryl halides with thioacetamide
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The carbon-sulfur coupling reaction of aryl halides with thioacetamide using an MCM-41-immobilized bidentate nitrogen copper(I) complex [MCM-41-2N-CuI] as an efficient heterogeneous catalyst is described. Developed catalytic system is found to be effective for the coupling reaction of aryl halides with thioacetamide providing moderate to high yield of diaryl sulfides. This heterogeneous copper catalyst exhibits higher activity than CuI and can be recovered by a simple filtration of the reaction solution and reused for at least 10 consecutive trials without any decreases in activity.
- Cai, Mingzhong,Yao, Ruiya,Chen, Lin,Zhao, Hong
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p. 349 - 354
(2015/01/09)
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- A copper-catalyzed synthesis of symmetrical diarylsulfanes
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A room-temperature, copper-catalyzed synthesis of symmetrical diarylsulfanes has been developed. The reaction proceeds from aryl iodides and elemental sulfur (S8) by the action of copper(I) salts in the presence of N-ethyl-N-isopropylpropan-2-amine to afford the corresponding diarylsulfanes in good yields. Georg Thieme Verlag Stuttgart New York.
- Yavari, Issa,Ghazanfarpour-Darjani, Majid,Solgi, Yazdan
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p. 1121 - 1123
(2014/05/20)
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- Use of base control to provide high selectivity between diaryl thioether and diaryl disulfide for C-S coupling reactions of aryl halides and sulfur and a mechanistic study
-
Previous studies have reported that S-arylation produces diaryl disulfide when the precursors include sulfur powder and aryl halide using CuI as the catalyst. However, our research has revealed that the use of different bases in the above S-arylation process results in the coproduction of diarylsulfane and diaryldisulfane. In addition, we have demonstrated that the ratio of the two products can be controlled by selecting the alkalinity of the bases. 1H NMR spectra showed that diaryldisulfane was the first product, which became the reagent in a reaction with aryl halide to form diarylsulfane through CuI catalysis. Various aryl halides were tested to enhance the selectivity between diarylsulfane and diaryldisulfane using various different bases, leading to the following principles. A weak base, such as metal carbonate or acetate, results in the production of only diaryldisulfane; a strong base, such as metal hydroxide, results in the production of both diaryldisulfane and diarylsulfane. According to DFT calculations, hydroxide ions, which were exchanged for iodide and bonded with Cu, affected Cu electrons more strongly to reduce diaryl disulfide.
- Chen, Hsing-Ying,Peng, Wei-Te,Lee, Ying-Hsien,Chang, Yu-Lun,Chen, Yen-Jen,Lai, Yi-Chun,Jheng, Nai-Yuan,Chen, Hsuan-Ying
-
p. 5514 - 5522
(2013/11/06)
-
- No-carrier-added [18F]fluoroarenes from the radiofluorination of diaryl sulfoxides
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No-carrier-added [18F]fluoroarenes were synthesized through the radiofluorination of diaryl sulfoxides with [18F]fluoride ion. Diaryl sulfoxides bearing a para electron-withdrawing substituent readily gave the corresponding 4-[18F]fluoroarenes in high RCYs. This process broadens the scope for preparing novel 18F-labeling synthons and PET radiotracers.
- Chun, Joong-Hyun,Morse, Cheryl L.,Chin, Frederick T.,Pike, Victor W.
-
supporting information
p. 2151 - 2153
(2013/03/14)
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- Rhodium-catalyzed synthesis of diaryl sulfides using aryl fluorides and sulfur/organopolysulfides
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Substituted pentafluorobenzenes react with sulfur to give bis(4-substituted 2,3,5,6-tetrafluorophenyl) sulfides in the presence of RhH(PPh 3)4, 1,2-bis(diphenylphosphino)benzene (dppBz), and tributylsilane. The reaction proceeds efficiently between room temperature and 80 °C. A comparative study of the reactivities of an organic trisulfide and a tetrasulfide showed notable substrate specificity. Di-tert-butyl tetrasulfide reacted with reactive aryl monofluorides and substituted pentafluorobenzenes. Di-tert-butyl trisulfide reacted with aryl monofluorides. The reactivity was explained on the basis of the difference in S-S bond energy.
- Arisawa, Mieko,Ichikawa, Takuya,Yamaguchi, Masahiko
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p. 5318 - 5321
(2013/01/15)
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- Ligand-free copper-catalyzed synthesis of diaryl thioethers from aryl halides and thioacetamide
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Diaryl thioethers can be prepared via a copper-catalyzed cross-coupling between aryl halides and thioacetamide using Cs2CO3 as a base and DMSO-H2O as a solvent at 120 °C. Georg Thieme Verlag Stuttgart - New York.
- Tao, Chuanzhou,Lv, Aifeng,Zhao, Nan,Yang, Shuai,Liu, Xiaolang,Zhou, Jian,Liu, Weiwei,Zhao, Jing
-
supporting information; experimental part
p. 134 - 138
(2011/03/22)
-
- Palladium-catalyzed C-S coupling: Access to thioethers, benzo[b]thiophenes, and thieno[3,2-b]thiophenes
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The first C-S bond formation/cross-coupling/cyclization domino reaction using thiourea as a cheap and easy to handle dihydrosulfide surrogate has been developed. Structurally important biarylthioether, benzo[b]thiophenes, and thieno[3,2-b]thiophene scaffolds are provided in high yield.
- Kuhn, Marius,Falk, Florian C.,Paradies, Jan
-
supporting information; experimental part
p. 4100 - 4103
(2011/10/08)
-
- Optimization of the central linker of dicationic bis-benzimidazole anti-MRSA and anti-VRE agents
-
A series of bis-benzimidazole diamidine compounds containing different central linkers has been synthesized and evaluated for in vitro antibacterial activities, including drug-resistant bacterial strains. Seven compounds have shown potent antibacterial activities. The anti-MRSA and anti-VRE activities of compound 1h were more potent than that of the lead compound 1a and vancomycin.
- Hu, Laixing,Kully, Maureen L.,Boykin, David W.,Abood, Norman
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scheme or table
p. 3374 - 3377
(2010/02/28)
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- Photoinduced nucleophilic substitution of aryl halides with potassium thioacetate - A one-pot approach to aryl methyl and diaryl sulfides
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Aryl methyl sulfides and diaryl sulfides were prepared by photoinduced reactions of potassium thioacetate with aryl halides under entrainment conditions. Without isolation, the arene thiolates obtained by the aromatic substitution were quenched with methyl iodide to afford the aryl methyl sulfides in 26-59% yields in a "one-pot" procedure together with the diaryl sulfides in variable yields (3-31 %). By optimization of the reaction conditions it was possible to improve the formation of the Ar2S, going from moderate to good yields (64-83%). Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Schmidt, Luciana C.,Rey, Valentina,Penenory, Alicia B.
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p. 2210 - 2214
(2007/10/03)
-
- One-Pot Two-Step Synthesis of Aryl Sulfur Compounds by Photoinduced Reactions of Thiourea Anion with Aryl Halides
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(Equation presented) The photoinduced reactions of aryl halides with the thiourea anion afford arene thiolate ions in DMSO. These species without isolation, and by a subsequent aliphatic nucleophilic substitution, S RN1 reaction, oxidation, or protonation, yield aryl methyl sulfides, diaryl sulfides, diaryl disulfides, and aryl thiols with good yields (50-80%). This is a simple and convenient approach which involves the use of the commercially available and inexpensive thiourea in a one-pot two-step process for the synthesis of aromatic sulfur compounds.
- Argueello, Juan E.,Schmidt, Luciana C.,Penenory, Alicia B.
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p. 4133 - 4136
(2007/10/03)
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- Bisoxadiazolidine derivative
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A bisoxadiazolidine dione derivative represented by the following general formula (I) or a pharmaceutically acceptable salt thereof, which is useful as an insulin sensitivity-increasing drug, and a pharmaceutical composition thereof. STR1 each represents a phenylene group L: (1) an oxygen, (2) a STR2 (3) a --S(O)n --, (4) a --CO--, (5) a STR3 (6) an alkylene group or an alkenylene group which may respectively be interrupted with an oxygen atom and/or a sulfur atom.
- -
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- Nucleophilic properties of thiourea towards aromatic halides
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Arylsulfides (and diaryldisulfides obtained spontaneously by oxidation of the arylsulfides during the work-up) and diarylsulfides can be obtained by substituting aryl radicals by the thiourea onion in liquid ammonia under an electrochemical inducement.
- Combellas,Dellerue,Mathey,Thiebault
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p. 539 - 542
(2007/10/03)
-
- Two efficient and practical syntheses of methyl 4-mercaptobenzoate
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Two efficient syntheses of methyl-4-mercaptobenzoate are described, one utilizing the dianion of 4-bromothiophenol, the other a S(N)Ar reaction starting with 4-fluorobenzonitrile.
- Tickner,Huang,Gombatz,Mills,Novack,Webb
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p. 2497 - 2505
(2007/10/02)
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- PHASE TRANSFER CATALYZED MELT SYNTHESIS OF DIARYL SULFIDES
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The phase transfer catalyzed interaction of sodium sulfide with molten aryl halides is described.The yields of diaryl sulfide are greater than 50percent when activating groups such as cyano, nitro, phthalimido, and anhydro are present on the aromatic ring.In the absence of these activating groups the yields are less than 2percent.The effect of parameters such as reaction temperature, reactant concentration and the nature of the phase transfer catalyst on the reaction yields are also reported.This procedure is especially useful for activated substrates that are sensitive to side reactions in dipolar aprotic solvents.
- Evans, Thomas L.
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p. 435 - 444
(2007/10/02)
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- Diaryl Sulfide Cleavage by Sodium Sulfide in Dipolar Aprotic Solvents
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The interaction of sodium sulfide with diaryl sulfides that possess electron-withdrawing substituents (e. g., cyano or nitro) on the aromatic rings results in cleavage of the thioether and the formation of sodium aryl sulfides in dipolar aprotic solvents.Exchange reactions between these diaryl sulfides and sodium aryl sulfides are also observed in dipolar aprotic solvents.The cleavage and exchange reactions were employed to prepare mixed diaryl or alkyl aryl sulfides from symmetrical diaryl sulfides.
- Evans, Thomas L.,Kinnard, Richard D.
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p. 2496 - 2499
(2007/10/02)
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