- Catalytic Reductive Cleavage of Poly(phenylene sulfide) Using a Hydrosilane
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The solvent-insoluble poly(phenylene sulfide) main chain was reductively cleaved by using triethylsilane as a hydrogen source under palladium/I c Hex catalytic conditions. After the reaction, benzene and bis(triethylsilyl) sulfide as a sulfide source were formed efficiently. This method could be operated on a gram scale.
- Minami, Yasunori,Matsuyama, Nao,Matsuo, Yasuaki,Tamura, Masanori,Sato, Kazuhiko,Nakajima, Yumiko
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supporting information
p. 3351 - 3354
(2021/07/17)
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- Method for synthesizing asymmetric sulfide from molecular oxygen oxidation water phase under catalysis of water-soluble transition metal compound
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Aiming at problems that in the prior art organic solvent pollution can be caused and a great number of reaction byproducts are generated when asymmetric sulfides are prepared, the invention disclosesa method for synthesizing an asymmetric sulfide from a molecular oxygen oxidation water phase under catalysis of a water-soluble transition metal compound. The method comprises the following steps: dispersing a sulfydryl compound and a hydrazine compound as substrates in a mole ratio of 1:1 into an alkali solution, and at 40-100 DEG C, in the presence of oxygen, and with a water-soluble transitionmetal compound as a catalyst, stirring to carry out reactions, thereby obtaining the asymmetric sulfide. By adopting the method, molecular oxygen is adopted as an oxidant, and water is adopted as a solvent, so that an organic solvent is avoided, a high yield can be achieved, and the problem of byproducts can be generally avoided.
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Paragraph 0085-0088
(2019/07/29)
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- Surfactant-Type Catalyst for Aerobic Oxidative Coupling of Hydrazine with Thiol in Water
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A series of PEG-functionalized nitrogen ligands were developed to conduct an aerobic oxidative cross-coupling reaction between alkyl- or aryl-hydrazines with thiols in water. This surfactant-type catalyst enables high efficiencies and selectivities, while tolerating a large variety of functional groups. The mother liquor is still catalytically active after five runs.
- Ren, Xuanhe,Tang, Shanyu,Li, Longjia,Li, Jiao,Liang, Helong,Li, Ganzhong,Yang, Guanyu,Li, Heng,Yuan, Bingxin
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p. 8683 - 8690
(2019/07/08)
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- Alkyl Sulfides as Promising Sulfur Sources: Metal-Free Synthesis of Aryl Alkyl Sulfides and Dialkyl Sulfides by Transalkylation of Simple Sulfides with Alkyl Halides
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A site-selective metal-free dealkylative approach to synthesize aryl alkyl and symmetrical dialkyl sulfides has been developed. This procedure is convenient and has wide functional group tolerance giving rise to sulfides carrying various alkyl chains from simple alkyl sulfides and alkyl halides in good to excellent yields. This transalkylation proceeds by an ionic mechanism via sulfonium intermediates and it was proposed that dimethylacetamide (DMAC) may participate in part to promote the reaction.
- Liu, Ting,Qiu, Renhua,Zhu, Longzhi,Yin, Shuang-Feng,Au, Chak-Tong,Kambe, Nobuaki
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supporting information
p. 3833 - 3837
(2018/12/05)
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- Synergetic Effect of Monomer Functional Group Coordination in Catalytic Insertion Polymerization
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PhS- and PhNH-functionalized dienes are copolymerized efficiently with butadiene to stereoregular copolymers by [(mesitylene)Ni(allyl)][BArF4] (Ni-1). Overall polymerization rates and comonomer incorporations depend strongly on the l
- Leicht, Hannes,G?ttker-Schnetmann, Inigo,Mecking, Stefan
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supporting information
p. 6823 - 6826
(2017/05/31)
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- CuI promoted sulfenylation of organozinc reagents with arylsulfonyl chlorides
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A CuI promoted sulfenylation of organozinc reagents with arylsulfonyl chlorides/PPh3 has been explored. This reaction proceeded smoothly through an alkyl/aryl radical (generated from organometallics) under mild conditions and produced the desired sulfide products in excellent yields.
- Fu, Ying,Su, Yuhu,Xu, Qin-Shan,Du, Zhengyin,Hu, Yulai,Wang, Ke-Hu,Huang, Danfeng
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p. 6018 - 6022
(2017/02/05)
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- Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers
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Direct synthesis of NH-sulfoximines from sulfides has been achieved through O and NH transfer in the same reaction, occurring with complete selectivity. The reaction is mediated by bisacetoxyiodobenzene under simple conditions and employs inexpensive N-so
- Tota, Arianna,Zenzola, Marina,Chawner, Stephen J.,John-Campbell, Sahra St,Carlucci, Claudia,Romanazzi, Giuseppe,Degennaro, Leonardo,Bull, James A.,Luisi, Renzo
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supporting information
p. 348 - 351
(2017/01/03)
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- One-Pot Copper-Catalysed Thioetherification of Aryl Halides Using Alcohols and Lawesson's Reagent in Diglyme
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A new protocol for the thioetherification of structurally varied alcohols with aryl halides using Lawesson's reagent, catalysed by copper(I) iodide, and using diglyme as a safe solvent was developed. Using this method, the reactions of aryl halides proceeded efficiently, and the desired sulfides were obtained in high to excellent yields. The method uses alcohols as starting materials, which is a significant advantage over methods that start from thiols. Alcohols are widely commercially available in a much greater structural diversity than thiols, and they are also nontoxic and not foul-smelling. A reaction mechanism was proposed. A copper-catalysed method for the thioetherification of alcohols with aryl halides using Lawesson's reagent was developed.
- Gholinejad, Mohammad
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p. 4162 - 4167
(2015/06/30)
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- Magnetic nanoparticle-supported Pd(II)-cryptand 22 complex: An efficient and reusable heterogeneous precatalyst in the Suzuki-Miyaura coupling and the formation of aryl-sulfur bonds in honor and memory of late Prof. Mathias Mertes
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In the present work, silica-coated magnetic nanoparticles [Fe3O4@SiO2@C22-Pd(II)] were prepared and characterized by transmission electron microscopy, Fourier transform infrared spectroscopy, vibrating sample magnetometer, energy dispersive X-ray analysis, X-ray photoelectron spectroscopy, elemental analysis, inductively coupled plasma, thermogravimetric and differential thermal analysis. This heterogeneous catalyst is utilized as an effective catalyst for the Suzuki-Miyaura coupling of arylboronic acids and aryl halides, and the cross-coupling reaction of aryl halides and thiols. The catalyst was easily separated by magnetic decantation and the recovered catalyst was reused for five cycles without any significant loss of the catalytic activity.
- Movassagh, Barahman,Takallou, Ahmad,Mobaraki, Akbar
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- High surface and magnetically recoverable mPANI/pFe3O 4 nanocomposites for C-S bond formation in water
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A high surface area mPANI/pFe3O4 nanocomposite from mesoporous polyaniline and porous magnetic Fe3O4 was used as a catalyst in the S-arylation of thiophenol with aryl chlorides and in the C-S bond formation between aryl iodides and thiourea in water. The mesoporosity of the polyaniline enhances the efficiency and stability of the porous magnetic Fe3O4 nanoparticles in both coupling reactions. The mPANI/pFe3O4 nanocomposite can be recovered with an external magnet and reused several times due to the superparamagnetic nature of the porous Fe3O4 nanoparticles.
- Damodara,Arundhathi,Likhar, Pravin R.
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p. 797 - 802
(2013/04/10)
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- Enantioselective nitrene transfer to sulfides catalyzed by a chiral iron complex
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Iron works: Enantioselective nitrene transfer to sulfide was accomplished by a chiral iron(III)/PyBOX catalyst (see scheme). Various sulfimides were thus obtained in high enantioselectivities and yields. Applications of this protocol to the syntheses of enantioenriched sulfoximines and an epoxide were also demonstrated. Copyright
- Wang, Jun,Frings, Marcus,Bolm, Carsten
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supporting information
p. 8661 - 8665
(2013/09/12)
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- Gas-phase S-alkylation of benzenethiol with aliphatic alcohols, ethers, esters, alkyl halides and olefins over halide cluster catalysts of Groups 5 and 6 transition metals
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Benzenethiol was reacted with methanol under a hydrogen stream over [(Nb6Cl12)Cl2(H2O) 4]·6H2O supported on silica gel. Catalytic activity of the cluster commenced above 250 °C, yielding methyl phenyl sulfide. The selectivity was 98% at 400 °C. Molybdenum, tantalum and tungsten halide clusters with the same octahedral metal framework also catalyzed the reaction. Primary alcohols with shorter alkyl chains were effective reagents for the S-alkylation. Aliphatic ethers, dialkyl carbonates, orthoesters and alkyl halides were effective reagents for the S-alkylation. When 1-hexene was applied to the reaction, spontaneous and catalytic S-alkylation proceeded simultaneously above 200 °C, yielding n-hexyl phenyl sulfide. When alkyl acetates were subjected to this reaction, the niobium cluster afforded S-phenyl thioacetate, and the other clusters afforded alkyl phenyl sulfides selectively. A Br?nsted acid site attributable to a hydroxo ligand, which is formed on the cluster complex by thermal activation, is proposed as the active site of the catalysts.
- Nagashima, Sayoko,Kudo, Kentaro,Yamazaki, Hitomi,Kamiguchi, Satoshi,Chihara, Teiji
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- Efficient recyclable CuI-nanoparticle-catalyzed S-arylation of thiols with aryl halides on water under mild conditions
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CuI nanoparticles efficiently catalyzed the C-S cross coupling of aryl and alkyl thiols with aryl halides in the absence of ligands on water under mild conditions. A wide range of diaryl sulfides and aryl alkyl sulfides are synthesized in good to excellent yields utilizing this protocol. This procedure is particularly noteworthy given its mild conditions, avoiding the undesired formation of disulfides through oxidation of thiols. The recovery and successful reutilization of the catalyst is described. Furthermore, the directed synthesis of bisarylated product is presented. The Royal Society of Chemistry 2012.
- Xu, Hua-Jian,Liang, Yu-Feng,Zhou, Xin-Feng,Feng, Yi-Si
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supporting information; experimental part
p. 2562 - 2568
(2012/04/23)
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- Nano-CuFe2O4 as a magnetically separable and reusable catalyst for the synthesis of diaryl/aryl alkyl sulfides via cross-coupling process under ligand-free conditions
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An efficient protocol was developed for the CuFe2O4 nanopowder-catalyzed aryl-sulfur bond formation between aryl halide and thiol/disulfide. A variety of aryl sulfides were synthesized in impressive yields with good chemoselectivity and functional group tolerance in the presence of a catalytic amount of CuFe2O4, Cs2CO 3 as base, in nitrogen atmosphere, under ligand-free conditions, in DMSO as solvent at 100 °C. The catalyst is air-stable, inexpensive, magnetically separable and recyclable up to four cycles.
- Swapna, Kokkirala,Murthy, Sabbavarapu Narayana,Jyothi, Mocharla Tarani,Nageswar, Yadavalli Venkata Durga
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experimental part
p. 5989 - 5996
(2011/10/08)
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- One-pot synthesis of symmetrical and unsymmetrical aryl sulfides by Pd-catalyzed couplings of aryl halides and thioacetates
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Aryl sulfides were obtained from the coupling reaction of S-aryl (or S-alkyl) thioacetates and aryl bromides in the presence of palladium catalyst. This reaction method enables the one-pot synthesis of symmetrical and unsymmetrical diaryl sulfides by employing potassium thioacetate with aryl iodides and aryl bromides.
- Park, Namjin,Park, Kyungho,Jang, Mihee,Lee, Sunwoo
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experimental part
p. 4371 - 4378
(2011/07/06)
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- One-pot reduction of sulfoxides with NaBH4, CoCl2. 6H2O catalyst, and moist alumina
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Sulfoxides are reduced by a combination of sodium borohydride, a catalytic amount of cobalt(II) chloride hexahydrate, and chromatographic neutral alumina preloaded with a small amount of water (moist alumina) in hexane to produce the corresponding sulfides in good to excellent yields under mild conditions. An interesting structural influence of sulfoxides on their reactivity is observed. Copyright
- Yakabe, Shigetaka,Hirano, Masao,Morimoto, Takashi
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experimental part
p. 2251 - 2255
(2011/06/27)
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- Silica nanoparticles as a reusable catalyst: A straightforward route for the synthesis of thioethers, thioesters, vinyl thioethers and thio-Michael adducts under neutral reaction conditions
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A simple and straightforward route for the synthesis of thioethers, thioesters, vinyl thioethers and thio-Michael adducts has been demonstrated using silica nanoparticles (NPs) as a reusable catalyst via the 1,2-addition of thiols to alkenes, alkynes and alkyl/acyl halides, and the 1,4-addition of thiols to conjugated alkenes at room temperature.
- Banerjee, Subhash,Das, Jayanta,Alvarez, Richard P.,Santra, Swadeshmukul
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experimental part
p. 302 - 306
(2010/06/13)
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- Improvement of pharmacological properties of irreversible thyroid receptor coactivator binding inhibitors
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We have previously reported the discovery and preliminary structure activity relationships of a series of β-aminoketones that disrupt the binding of coactivators to TR. However, the most active compounds had moderate inhibitory potency and relatively high cytotoxicity, resulting in narrow therapeutic index. Additionally, preliminary evaluation of in vivo toxicology revealed a significant dose related cardiotoxicity. Here we describe the improvement of pharmacological properties of thyroid hormone receptor coactivator binding inhibitors. A comprehensive survey of the effects of substitutents in key areas of the molecule was carried out based on mechanistic insight from the earlier report. This study revealed that both electron withdrawing and hydrophobic substituents on the aromatic ring led to higher potency. On the other hand, moving from an alkyl to a sulfonyl alkyl side chain led to reduced cytotoxicity. Finally, utilization of amine moieties having low pKa's resulted in lowered ion channel activity without any loss of pharmacological activity.
- Jong, Yeon Hwang,Arnold, Leggy A.,Zhu, Fangyi,Kosinski, Aaron,Mangano, Thomas J.,Setola, Vincent,Roth, Bryan L.,Guy, R. Kiplin
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supporting information; experimental part
p. 3892 - 3901
(2010/02/17)
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- Native silica nanoparticle catalyzed anti-Markovnikov addition of thiols to inactivated alkenes and alkynes: a new route to linear and vinyl thioethers
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A new route for the synthesis of linear and vinyl thioethers has been demonstrated using bare silica nanoparticle as catalyst at room temperature under solvent-free conditions. The catalyst can be reused up to six times without loss of catalytic activity.
- Banerjee, Subhash,Das, Jayanta,Santra, Swadeshmukul
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scheme or table
p. 124 - 127
(2009/04/14)
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- Water-promoted highly selective anti-Markovnikov addition of thiols to unactivated alkenes
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The highly selective anti-Markovnikov addition of thiols to unactivated alkenes is demonstrated in water at room temperature without any additive. This is a very simple and efficient method for the synthesis of linear thioethers. Georg Thieme Verlag Stuttgart.
- Ranu, Brindaban C.,Mandal, Tanmay
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p. 925 - 928
(2008/02/02)
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- Efficient CuO-nanoparticle-catalyzed C-S cross-coupling of thiols with iodobenzene
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Cheap but good: Readily available CuO nanoparticles are not only less expensive than other catalysts used for the C-S cross-coupling of thiols with aryl halides, but they are also effective at a moderate temperature and low concentration. The title reaction proceeds with a variety of alkyl and aryl thiols to give the corresponding sulfides in high yields (see scheme).
- Rout, Laxmidhar,Sen, Tamal K.,Punniyamurthy, Tharmalingam
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p. 5583 - 5586
(2008/03/18)
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- Arylation of n-hexylthiol and n-hexyl phenyl sulfide using diphenyliodonium triflate: Synthetic and mechanistic aspects - Application to the transformation of n-hexylthiol to n-hexylselenide
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n-Hexyl diphenylsulfonium triflate has been efficiently prepared from n-hexylthiol and diphenyliodonium triflate and has been efficiently transformed to n-hexyl selenide. Georg Thieme Verlag Stuttgart.
- Krief, Alain,Dumont, Willy,Robert, Michael
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p. 484 - 486
(2007/10/03)
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- Synthesis of primary-alkyl selenols and selenides from primary-alkyl thiols involving diphenyl sulfonium salts
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Hexyl thiol has been transformed to hexyl selenol and related selenides and selenocyanate by substitution of the corresponding hexyldiphenylsulfonium tetrafluoroborate with selenium nucleophiles. The Royal Society of Chemistry 2005.
- Krief, Alain,Dumont, Willy,Robert, Michael
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p. 2167 - 2168
(2007/10/03)
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- Reductive cleavage of S-S bond by Zn/AlCl3 system: A novel method for the synthesis of sulfides from alkyl tosylates and disulfides
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Alkyl and aryl disulfides are reduced by zinc powder in the presence of AlCl3 in aqueous media to yield zinc thiolates. These thiolate anion species then react with alkyl tosylates to give sulfides in high to excellent yields.
- Movassagh, Barahman,Mossadegh, Amir
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p. 2337 - 2343
(2007/10/03)
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- Reductive cleavage of S-S bond by Zn/AlCl3 system: A novel method for the synthesis of sulfides from alkyl tosylates and disulfides
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Alkyl and aryl disulfides are reduced by zinc powder in the presence of AlCl3 in aqueous media to yield zinc thiolates. This thiolate anion species then react with alkyl tosylates to give sulfides in high execellent yields.
- Movassagh, Barahman,Mossadegh, Amir
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p. 1685 - 1690
(2007/10/03)
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- Co-C bond cleavage in the reactions of alkyl, benzyl and heteroaromaticmethyl cobaloximes with arene sulfenyl chloride: Homolytic and heterolytic pathways
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The reactions of arene sulfenyl chlorides, ArSCl, (Ar=Ph, C6Cl5, 2,4 (NO2)2C6H3) with organocobaloximes, RCo(dmgH)2Py, (R=alkyl, benzyl and heteroaromaticmethyl) were carried out under thermal and photochemical conditions. A variety of organic and organometallic products are formed depending upon the substrate cobaloxime. For 3-methoxybenzyl and heteroaromaticmethyl cobaloximes the results suggest that they represent a unique class of cobaloximes whereby both the aromatic ring as well as the Co-C bond are highly activated towards attack by the arene sulfenyl chloride. Both homolytic as well as heterolytic pathways are operative.
- Gupta,Dixit, Vandana,Das, Indira
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- Anti-Markovnikov addition of thiols across double bonds catalyzed by H- Rho-zeolite
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A variety of olefins react with thiols in the presence of a catalytic amount of H-Rho-zeolite to afford the corresponding anti-Markovnikov addition products in good to excellent yields.
- Kumar, Pradeep,Pandey, Rajesh Kumar,Hegde, Vishnumurthy R.
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p. 1921 - 1922
(2007/10/03)
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- Reductive Cleavage of the S-Si Bond in Arylsulfanyltrimethylsilanes: A Novel Method for the Synthesis of Unsymmetrical Sulfides
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Arylsulfanyltrimethylsilanes are reduced by samarium diiodide to yield samarium arylthiolates which react with alkyl halides to give unsymmetrical sulfides.
- Zhang, Songtin,Zhang, Yongmin M.
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- Kinetics of Intramolecular Alkyl Radical Attack on Sulfur in Disulfides and Thioesters
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The 4-(alkyldithio)butyl radicals 8a and c, and the 4-(phenyldithio)butyl radical 8b, generated from the corresponding esters of N-hydroxypyridine-2(1H)-thione, undergo fast exo-cyclisation by SHi attack at sulfur.Similarly, the 5-(alkyldithio)pentyl radical 8d undergoes 1,6-ring formation.The rate constants for cyclisation were determined by photolysis of the radical precursors in the presence of appropriate thiols.Butyl and pentyl radicals bearing ω-acetylthio or ω-benzoylthio substituents also undergo ring closure but much more slowly.The kinetics of these intramolecular SH2 reactions are discussed and compared with those for the intermolecular attack of hexyl radicals on diphenyl disulfide and on dibutyl disulfide.
- Beckwith, Athelstan L. J.,Duggan, Sandhya A. M.
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p. 1509 - 1518
(2007/10/02)
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- THE HYDROGENOLYSIS OF ORGANIC HALIDES WITH ZINC DUST IN MICELLE
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A simple and useful synthetic procedure for hydrogenolysis of organic halides with zinc dust in micellar media is described.
- Jursic, Branko,Galosi, Andreja
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p. 1649 - 1654
(2007/10/02)
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- Reactions of Alkylmercurials with Heteroatom-Centered Acceptor Radicals
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The relative reactivities of alkylmercury halides toward PhS., PhSe., or I. decrease drastically from R = tert-butyl to R = sec-alkyl to R = n-butyl, indicative that R. is formed in the rate-determining step in the attack of these radicals upon RHgCl.The alkyl radicals thus formed will enter into chain reactions in which a heteroatom-centered radical (A.) is regenerated from substrates such as RS-SR, ArSe-SeAr, ArTe-TeAr, PhSe-SO2Ar, Cl-SO2Ph; ZCH=CHA (A = Cl, I, SPh, SO2Ph); or PhCCHA (A = I, SPh, SO2Ph). β-Styrenyl (PhCH=CHA, Ph2C=CHA) and β-phenethynyl (PhCCA) systems with A = I, Br, SO2Ph also enter into chain reactions with mercury(II) salts with the ligands PhS, PhSe, PhSO2, or (EtO)2PO.The relative reactivities of a series of reagents toward t-Bu. and of PhCH=CHA, Ph2C=CHA, and PhCCA toward c-C6H11. are reported as well as the regioselectivity of t-Bu. attack observed for 1,2-disubstituted ethylenes (ZCH=CHA) with Z and A from the group Ph, Cl, Br, I, SO2Ph, SPh, Bu3Sn.Reactions of (E)- and (Z)-PhCH=CHI or MeO2CCH=CHI with t-Bu. or c-C6H11. occurred in a regioselective and stereospecific (retention) manner.Reactions of (E)- and (Z)-ClCH=CHCl occurred in a nonstereospecific manner in which the E/Z product ratio increased with the bulk of the attacking radical.A similar effect on the E/Z product ratios was observed for (Z)-MeO2CCH=CHCl.
- Russell, Glen A.,Ngoviwatchai, Preecha,Tashtoush, Hasan I.,Pla-Dalmau, Anna,Khanna, Rajive K.
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p. 3530 - 3538
(2007/10/02)
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- ONE-POT SYNTHESIS OF ALKYL ARYL TRITHIOCARBONATES FROM BENZENETHIOLS, ALKYL HALIDES, AND CARBON DISULFIDE WITH A PHASE-TRANSFER CATALYST.
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Various alkyl aryl trithiocarbonates may readily be synthesized in good yield at low temperatures such as 20 degree C by allowing trioctylmethylammonium chloride (phase-transfer catalyst) to catalyze reaction of benzenethiols and alkyl halides with carbon disulfide.
- Sugawara,Shirahata,Sato,Sato
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p. 3353 - 3354
(2007/10/02)
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- Determination of Sulfur in Asphalts by Selective Oxidation and Photoelectron Spectroscopy for Chemical Analysis
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The characterization of sulfur in asphalts is investigated by coupling selective reactions and photoelectron spectroscopy for chemical analysis.The specificity of the two following reactions has been studied on test compounds: oxidation of sulfides with tert-butyl hydroperoxide in chloroform (a); reduction by lithium aluminum hydride of sulfones in tetrahydrofuran (b).These reactions have been used with an asphalt, directly for (a) or after a preoxidation with m-chloroperbenzoic acid for (b) to determine, using photoelectron spectroscopy, which kind of sulfur was invol ved.An analytical scheme sums up the different results: cyclic sulfides = 67percent, thiophenic sulfides = 54percent, cyclanic sulfide = 13percent, alkyl and aryl alkyl sulfides = 33percent.
- Ruiz, Jean-Michel,Carden, Brian M.,Lena, Louis J.Vincent, Emile-Jean,Escalier, Jean-Claude
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p. 688 - 691
(2007/10/02)
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- A Two-stage Conversion of Primary-alkyl Primary-amines into Alcohols and Further Examples of Transfunctionalisation of Amines under Mild Conditions
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Phase-transfer catalysts allow the conversion of primary-alkyl primary-amines into primary alcohols, sulphones, sulphides, and ethers at = 100 deg C via the pentacyclic pyridiniums (9).
- Katritzky, Alan R.,Saba, Antonio,Patel, Ranjan C.
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p. 1492 - 1494
(2007/10/02)
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