103-19-5Relevant articles and documents
Nickel Schiff-base complexes immobilized on boehmite nanoparticles and their application in the oxidation of sulfides and oxidative coupling of thiols as novel and reusable nano organometal catalysts
Ghorbani-Choghamarani, Arash,Tahmasbi, Bahman,Arghand, Fatemeh,Faryadi, Sara
, p. 92174 - 92183 (2015)
Boehmite nanoparticles were prepared by very simple and inexpensive procedure in water at room temperature using commercially available materials. Two Schiff-base complexes of nickel have been immobilized on the boehmite nanoparticles. These catalysts were characterized by FT-IR spectroscopy, TGA, XRD, BET, UV-DRS, TEM, SEM, EDS and ICP-OES techniques. These compounds were applied as catalysts for the oxidation of sulfides to sulfoxides and oxidative coupling of thiols to disulfides under mild reaction conditions at room temperature. These catalysts were recovered by simple filtration and reused several times without significant loss of their catalytic efficiency.
Kice,Favstritsky
, p. 114 (1970)
Heterogeneously Ni-Pd nanoparticle-catalyzed base-free formal C-S bond metathesis of thiols
Mitamura, Kanju,Yatabe, Takafumi,Yamamoto, Kidai,Yabe, Tomohiro,Suzuki, Kosuke,Yamaguchi, Kazuya
, p. 3749 - 3752 (2021)
This study rationally designed a heterogeneously catalyzed system (i.e., using Ni-Pd alloy nanoparticles supported on hydroxyapatite (Ni-Pd/HAP) under an H2atmosphere) achieving an efficient base-free formal C-S bond metathesis of various thiolsviasuppression of the Ni catalysis deactivation.
Fe3O4@S-ABENZ@VO: Magnetically separable nanocatalyst for the efficient, selective and mild oxidation of sulfides and oxidative coupling of thiols
Rezaei, Somaieh,Ghorbani-Choghamarani, Arash,Badri, Rashid,Nikseresht, Ahmad
, (2018)
Oxovanadium(IV) immobilized on Fe3O4@S-ABEN is reported as a highly efficient nanocatalyst for the oxidation of sulfides and oxidative coupling of thiols (using H2O2 as green oxidant), the products of which are obtained in high to excellent yields. The products can be separated by a simple extraction with organic solvent and the catalyst is highly efficient, especially in terms of selectivity of desired product. The catalytic system can be recycled and reused without significant loss of catalytic activity.
Flavin/I2-Catalyzed Aerobic Oxidative C–H Sulfenylation of Aryl-Fused Cyclic Amines
Jiang, Xinpeng,Zhao, Zongchen,Shen, Zhifeng,Chen, Keda,Fang, Liyun,Yu, Chuanming
, p. 3889 - 3895 (2020)
We report an aerobic oxidative C–H sulfenylation of aryl-fused cyclic amines with various thiols catalyzed by flavin/I2 for the first time. While flavin I catalyzed the C–H sulfenylation of indolines to afford 3-sulfenylindoles, flavin II enabl
Biomimetic methane generation and disulfide formation by catalysis with a nickel complex
Tada, Masaru,Masuzawa, Yoshihide
, p. 2161 - 2162 (1997)
The final metabolic process of methanogen, methane generation and simultaneous disulfide formation, is simulated by the reaction of thioanisole with a toluenethiyl radical in the presence of a nickel complex, which is generated by the photolysis of a toluenethiolato-nickel complex.
NEW REAGENTS 4. REDUCTION OF SULPHONYL CHLORIDES AND SULPHOXIDES WITH ALUMINIUM IODIDE
Babu, J. Ramesh,Bhatt, M. Vivekananda
, p. 1073 - 1074 (1986)
Aluminium iodide reduces sulphonyl chlorides to disulphides and sulphoxides to sulphides under mild conditions in acetonitrile.
Green preparation of disulfides from corresponding thiols by poly(4-vinylpyridinium nitrate) as recoverable and new polymeric reagent
Ghorbani-Choghamarani, Arash,Sardari, Sara
, p. 63 - 69 (2011)
Poly(4-vinylpyridinium nitrate) was found to be a recyclable and highly efficient oxidizing polymer for the oxidative coupling of a variety of aliphatic or aromatic thiols to the corresponding disulfides. Poly(4-vinylpyridinium nitrate) is an extremely mild agent, which gave no other oxidized side products.
Consecutive O?S/N?S Bond Cleavage in Gold-Catalyzed Rearrangement Reactions of Alkynyl N-Sulfinylimines
Tashiro, Hiroki,Terada, Masahiro,Nakamura, Itaru
, p. 12248 - 12252 (2021)
Gold-catalyzed reactions of alkynyl N-sulfinylimines were used to produce the corresponding 2H-azirines possessing sulfenyl and acyl groups at the 3-position of the azirine ring in good to excellent yields. These reactions involved internal transfer of the sulfinyl oxygen atom to form a thiooxime intermediate tethered to an α-oxo gold carbene moiety. Subsequent insertion of the carbene into the N?S bond resulted in ring construction.
A convenient method for reductive desulfonylation of β-ketosulfones with Sm/HgCl2 system
Guo, Hongyun,Zhang, Yongmin
, p. 2559 - 2564 (2000)
The Sm/HgCl2 system reduces β-ketosulfones to the corresponding ketones in moderate to good yield under mild conditions.
Synthetic Methods and Reactions. 93. Preparation of Disulfides via Iodotrimethylsilane-Mediated Reductive Dimerization of Sulfonyl Halides
Olah, George A.,Narang, Subhash C.,Field, Leslie D.,Salem, George F.
, p. 4792 - 4793 (1980)
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Fe3O4 MNPs-DETA/Benzyl-Br3: A new magnetically reusable catalyst for the oxidative coupling of thiols
Shiri, Lotfi,Kazemi, Mosstafa
, p. 1171 - 1176 (2017)
We report a new strategy to immobilize a bromine source on the surface of magnetic Fe3O4 nanoparticles (Fe3O4 MNPs-DETA/Benzyl-Br3) leading to amagnetically recoverable catalyst, which exhibits high catalytic efficiency in oxidative coupling of thiols to the disulfides (89–98%). The Fe3O4 MNPs-DETA/Benzyl-Br3 catalyst was fabricated by anchoring 3-chloropropyltrimethoxysilane (CPTMS) onmagnetic Fe3O4 nanoparticles, followed with N-benzylation and reaction with bromine in tetrachloridecarbon. The resulting nanocomposite was analyzed by a series of characterization techniques such as FT-IR, SEM, TGA, VSM and XRD. The catalyst could be recovered viamagnetic attraction and could be recycled at least 5 times without appreciable decrease in activity.
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Snyder,Geller
, p. 4864,4866 (1952)
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Solvent Controlled Transformation between Sulfonyl Hydrazides and Alkynes: Divergent Synthesis of Benzo[b]thiophene-1,1-dioxides and (E)-β-iodo Vinylsulfones
Ma, Yue,Wang, Kun,Zhang, Dong,Sun, Peng
, p. 597 - 602 (2019)
A green, efficient and controllable transformation between sulfonyl hydrazides and alkynes leading to benzo[b]thiophene-1,1-dioxides and (E)-β-iodo vinylsulfones via radical pathway has been developed. The reaction occurs rapidly in the presence of simply H2O2 and KI without the help of any transition metal. The chemoselectivity of the reaction is determined by the solvent in which the process is performed: TFE favors the cyclic product, while H2O medium generates the iodosulfonylative product. Notably, this protocol also represents the first direct approach to the aggregation-induced-emmision (AIE) active benzo[b]thiophene-1,1-dioxides from readily available sulfonyl hydrazides and alkynes in one step. (Figure presented.).
Atkins,Lentz
, p. 773 (1978)
Copper(I)-Promoted C-N Cross-Coupling of N-Heterocyclic Compounds with 1,2-Di(pyrimidin-2-yl) Disulfides
Wei, Kai-Jie,Quan, Zheng-Jun,Zhang, Zhang,Da, Yu-Xia,Wang, Xi-Cun
, p. 1743 - 1747 (2016)
A CuTC-promoted C-N cross-coupling of 1,2-di(pyrimidin-2-yl) disulfides with N-heterocyclic compounds including indoles, triazole benzotriazole, and benzoimidazole by C-S cleavage of the disulfides is reported.
Iodine- and PhI(OAc)2-Mediated Multicomponent Synthesis of (E)-1,3-Diphenyl-1-butene Derivatives
Marakalala, Mokgethwa B.,Kinfe, Henok H.
, p. 3311 - 3317 (2017)
A multicomponent reaction, promoted by molecular iodine and diacetoxyiodobenzene, for the synthesis of (E)-1,3-diphenyl-1-butene derivatives from styrene and thiophenol was developed. The attractiveness of the protocol is its ability to introduce a sulfur heteroatom without a need for an extra reaction step. The scope and limitations of the protocol are investigated.
Reaction of Organic Sulfur Compounds with Hyperoxide Anion (O2-anion radical). IV. Evidence for Formation of Peroxysulfur Intermediates: Oxidation of Sulfoxides, Phosphines, and Olefins with Intermediary Peroxysulfur Species
Oae, Shigeru,Takata, Toshikazu,Kim, Yong Hae
, p. 2712 - 2723 (1981)
Formations of peroxy-sulfenate(I), -sulfinate(II), and -sulfonate(III) as intermediates have been confirmed by stripping the peroxy oxygen with three kinds of trapping agents such as sulfoxides, phosphines, and olefins, added in the reaction systems of various organic sulfur compounds with hyperoxide anion (O2-anion radical).These sulfoxides, phosphines, and olefins were inert to O2-anion radical alone while electrophilic olefins, such as α,β-unsaturated ketones reacted readily with O2-anion radical to afford the carboxylic acid.Sulfoxides, added into the reaction system of disulfide, thiosulfinic S-ester, thiosulfonic S-ester, or sulfonyl chloride with O2-anion radical, were found to be oxidized to the sulfones with peroxysulfur intermediates formed in situ in the system.Phosphines, added into the reaction system of disulfide or sodium thiolate with O2-anion radical were also oxidized to the phosphine oxides.Not only stilbene and acenaphthylene but also chalcone and its derivatives, placed in the reactions of sulfonyl chloride, sulfinyl chloride and thiosulfonic S-ester with O2-anion radical were found to be oxidized to the corresponding epoxides.These observations suggest clearly that the intermediary peroxysulfur compounds can act as oxidizing agents which oxidize these trapping agents by the nucleophilic oxygenative oxidation.Similar intermediates were postulated and confirmed in the alkaline autoxidations of thiol and disulfide in which added phosphines and sulfoxides were also found to be oxidized to their oxides.The mechanisms of the reactions of these trapping agents with peroxysulfur intermediates are discussed.
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Klamann,Hofbauer
, p. 1489 (1952)
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Wardell et al.
, p. 25,28, 29 (1971)
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Minoura
, (1954)
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Cationic rhodium(I)/PPh3 complex-catalyzed dehydrogenation of alkanethiols to disulfides under inert atmosphere
Tanaka, Ken,Ajiki, Kaori
, p. 25 - 27 (2004)
A cationic rhodium(I)/PPh3 complex is an effective catalyst for dehydrogenation of primary or secondary alkanethiols to symmetrical disulfides under inert atmosphere. The dependence of reactivity on the structure of thiols is examined in detail.
Mild and highly efficient method for the oxidation of sulfides and oxidative coupling of thiols catalyzed by Fe3O4@MCM-41@VO-SPATB as efficient and magnetically recoverable nanocatalyst
Nikoorazm, Mohsen,Ghorbani, Farshid,Ghorbani-Choghamarani, Arash,Erfani, Zahra
, p. 553 - 562 (2019)
The use of oxo vanadium complex with s-propyl-2-aminobenzothioate ligand immobilized onto functionalized magnetic nanoporous MCM-41(Fe3O4@MCM-41@VO-SPATB) as efficient and magnetically recoverable nanocatalyst for oxidation of sulfides into sulfoxides and oxidative coupling of thiols into disulfides using H2O2 as green oxidant is presented. This method provides much improved modification of oxidation reactions in terms of mild reaction conditions, short reaction time and good-to-excellent yields of products. Another important feature of this method is the ability to reuse the magnetite nanocatalyst for several times with no loss of its catalytic activity.
Reactions of 1 aminothioxanthone 6,6 dioxides with formamide
Dusemund
, p. 230 - 234 (1975)
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Cyclization of N-Arylacrylamides via Radical Arylsulfenylation of Carbon-Carbon Double Bonds with Sulfonyl Hydrazides
Wang, Fu-Xiang,Tian, Shi-Kai
, p. 12697 - 12703 (2015)
An unprecedented tandem radical sulfenylation/cyclization reaction of N-arylacrylamides with sulfonyl hydrazides has been developed in the presence of iodine for the selective synthesis of 3-(sulfenylmethyl)oxindoles and 3-sulfenyl-3,4-dihydroquinolin-2(1H)-ones. Preliminary mechanistic studies showed that sulfonyl hydrazides decomposed completely at an early stage to thiosulfonates and disulfides, both of which underwent tandem radical sulfenylation/cyclization with N-arylacrylamides at a late stage.
Tetrabutylammonium Iodide Mediated Sulfenylation of Poly-substituted 1 H -Pyrazol-5-amines with Arylsulfonyl Hydrazides
He, Jing,Wei, Yueting,Li, Xuezhen,Dai, Bin,Liu, Ping
, p. 490 - 498 (2021/10/21)
A TBAI-mediated sulfenylation of N,3-diaryl-1-arylsulfonyl-1H-pyrazol-5-amines with arylsulfonyl hydrazides has been established, and an expanded inventory of N,5-diaryl-4-(arylthio)-1H-pyrazol-3-amines was constructed through C-S bond formation and N-S bond breaking. Mechanistic investigations suggest thiosulfonate as a key intermediate in the sulfenylation, and the detosylation is promoted by the generated arylsulfinic acid. The method is characterized by simple operating conditions, broad substrate range as well as gramscale reaction.
Copper acetate - Iodine co-mediated thiolation of 2-arylpyridines with thiophenol
He, Yayun,Hou, Senpeng,Hu, Junhao
, (2021/11/24)
Copper acetate - iodine co-mediated regioselective ortho-arylthiolation of 2-arylpyridines has been accomplished with inexpensive and convenient thiophenol as the arylthiolating reagent. This protocol features excellent functional group tolerance, generat
Paired Electrolysis Enabled Ni-Catalyzed Unconventional Cascade Reductive Thiolation Using Sulfinates
Kang, Jun-Chen,Li, Zi-Hao,Chen, Chao,Dong, Li-Kun,Zhang, Shu-Yu
supporting information, p. 15326 - 15334 (2021/10/25)
Herein, we have reported a nickel-catalyzed cascade reductive thiolation of aryl halides with sulfinates driven by paired electrolysis. This protocol uses sulfinates as the sulfur source, and various thioethers could be synthesized under mild conditions. By mechanism exploration, we find that a cascade chemical step is allowed on the electrode interface and could alter the reaction pathway in paired electrolysis, whose findings could help the discovery of novel cascade reactions with unique reactivity.
