- NFSI-catalyzed S[sbnd]S bond exchange reaction for the synthesis of unsymmetrical disulfides
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The metal-free S[sbnd]S bond exchange reaction of symmetrical disulfides catalyzed by NFSI is described. This novel protocol provides a facile and efficient approach to accessing important unsymmetrical disulfides. Furthermore, this strategy could also be utilized in the late-stage functionalization of amino acids, drugs, and natural products. The broad substrate scope, good functional group tolerance and easy accessibility of catalyst indicate that this strategy affords a green and practical complementary method to various unsymmetrical disulfides.
- Hu, Qingyue,Li, Zheng-Yi,Song, Mengjie,Sun, Xiaoqiang,Yang, Ke
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supporting information
(2022/01/26)
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- Method for NFSI-catalyzed synthesis of asymmetric disulphide derivatives
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The invention belongs to the field of fine chemical engineering, and relates to a method for NFSI-catalytically synthesizing an asymmetric disulphide derivative, which comprises the following steps: NFSI. The symmetric disulfide A and the symmetric disulf
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Paragraph 0018-0025; 0029
(2021/10/30)
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- Synthesis of unsymmetrical disulfides: Via PPh3-mediated reductive coupling of thiophenols with sulfonyl chlorides
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A facile and rapid synthesis of unsymmetrical aryl disulfides using PPh3-mediated reductive coupling of thiophenols with aryl sulfonyl chlorides was described. Good functional group tolerance and scalability were achieved in this strategy. More importantl
- Liang, Xiao,Pan, Yuanjiang,Wang, Dungai,Xiong, Mingteng,Zhou, Yifeng,Zhu, Heping
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supporting information
p. 4447 - 4451
(2020/10/20)
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- Alternating Current Electrolysis for the Electrocatalytic Synthesis of Mixed Disulfide via Sulfur–Sulfur Bond Metathesis towards Dynamic Disulfide Libraries
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A novel approach of electrolysis using alternating current was applied in the sulfur–sulfur bond metathesis of symmetrical disulfides towards unsymmetrical disulfides. As initially expected, a statistical distribution in disulfides was obtained. Furthermore, the influence of electrode polarisation by alternating current was investigated on a two-disulfide matrix. The highly dynamic nature of this chemistry resulted in the creation of dynamic disulfide libraries by expansion of the matrices, consisting of up to six symmetrical disulfides. In addition, mixing of matrices and stepwise expanding of a matrix by using alternating current electrolysis were realised.
- Hilt, Gerhard,Otten, Chris Josef,Sattler, Lars Erik
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supporting information
(2020/02/27)
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- Fenton-Inspired C-H Functionalization: Peroxide-Directed C-H Thioetherification
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Substoichiometric iron mediates the thioetherification of unactivated aliphatic C-H bonds directed by resident silylperoxides. Upon exposure to a catalytic amount of iron(II) triflate, TIPS-protected peroxides bearing primary, secondary, and tertiary C-H sites undergo chemoselective thioetherification of remote C-H bonds with diaryl disulfides. The reaction demonstrates a broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic experiments suggest that the reaction proceeds through 1,5-H atom abstraction by a hydroxyl radical generated with iron.
- Groendyke, Brian J.,Modak, Atanu,Cook, Silas P.
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p. 13073 - 13091
(2019/10/10)
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- Visible-Light-Induced Hydroxysulfurization and Alkoxysulfurization of Styrenes in the Absence of Photocatalyst: Synthesis of β-Hydroxysulfides and β-Alkoxysulfides
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We developed hydroxysulfurization and alkoxysulfurization of styrenes using a visible-light synthetic strategy in the absence of photocatalyst and oxidant. This strategy provided the corresponding β-hydroxysulfides and β-alkoxysulfides in moderate to good yields with high regioselectivity. The reaction was tolerated by a wide range of functional groups. This is the first example of ArSSAr/CBr4 system has been introduced into organic transformation. (Figure presented.).
- Ruan, Hongjie,Meng, Ling-Guo,Zhu, Lingqiong,Wang, Lei
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supporting information
p. 3217 - 3222
(2019/05/10)
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- Unsymmetrical Disulfides Synthesis via Sulfenium Ion
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An umpolung approach for the synthesis of unsymmetrical disulfides via sulfenium ion is reported. In situ generated electrophilic sulfenium ion from electron-rich thiols reacted with second thiols to yield unsymmetrical disulfides. Using an iodine catalyst and 4-dimethylaminopyridine (DMAP)/water as promoter, the target syntheses were achieved in one pot under aerobic condition.
- Parida, Amarchand,Choudhuri, Khokan,Mal, Prasenjit
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supporting information
p. 2579 - 2583
(2019/07/15)
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- A Novel Method for the Direct Synthesis of Symmetrical and Unsymmetrical Sulfides and Disulfides from Aryl Halides and Ethyl Potassium Xanthogenate
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An efficient and new method for the synthesis of disulfides and sulfides via the reaction of aryl halides with ethyl potassium xanthogenate in the presence of MOF-199 is described. O -Ethyl- S -aryl carbonodithioate has a key role as an intermediate in this procedure; it was converted into symmetrical diaryl disulfides in DMF. Additionally, this could be applied to the synthesis of unsymmetrical aryl alkyl(aryl′) disulfides by the reaction with S -alkyl(aryl) sulfurothioates (Bunte salts) as well as unsymmetrical aryl alkyl(aryl′) sulfides in DMSO.
- Soleiman-Beigi,Arzehgar
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supporting information
p. 986 - 992
(2018/02/09)
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- Aryl-alkyl asymmetric persulfate compound, and synthesis method and application thereof
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The invention discloses an aryl-alkyl asymmetric persulfate compound shown as a formula (3) and a synthesis method thereof. Arylboronic acid shown as a formula (I) and R2SSCOR3 shown as a formula (2) are used as reaction raw materials; under the effects of metal copper catalysts, reaction is performed to obtain the aryl-alkyl asymmetric persulfate compound. The method has the advantages that the reaction conditions are mild; the raw materials are low in cost and easy to obtain; the reaction operation is simple; the yield is higher; cheap metal is used as catalysts in the reaction process; economy and practicability are realized; the environment-friendly performance is achieved; reaction substrates can be easily prepared; after the reaction amplification, the reaction efficiency is high. The prepared aryl-alkyl asymmetric persulfate compound shown as the formula (3) and prepared by the method can be used for further synthesizing potential medicine compounds containing C-S bonds, such as benzyl (phenyl) thioether and benzyl (4-methoxy phenyl) thioether. The aryl-alkyl asymmetric persulfate compound and the synthesis method provided by the invention have the advantages of wide application prospects and practical value.
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Paragraph 0358; 0359; 0360; 0361
(2017/02/24)
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- Metal-free radical thiolations mediated by very weak bases
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Aromatic thioethers and analogous heavier chalcogenides were prepared by reaction of arene-diazonium salts with disulfides in the presence of the cheap and weak base NaOAc. The mild and practical reaction conditions (equimolar reagents, DMSO, r.t., 8 h) tolerate various functional groups (e.g. Br, Cl, NO2, CO2R, OH, SCF3, furans). Mechanistic studies indicate the operation of a radical aromatic substitution mechanism via aryl, acetyloxyl, thiyl, and dimsyl radicals.
- Koziakov, Denis,Majek, Michal,Jacobi Von Wangelin, Axel
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supporting information
p. 11347 - 11352
(2016/12/16)
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- Iron-catalysed Markovnikov hydrothiolation of styrenes
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The bis(triflimide)iron(III) salt catalyzes the hydrothiolation of styrenes in a Markovnikov fashion with good selectivities and high yields. After isolation, different benzylic thioethers are obtained. This iron(III) catalyst is unique in terms of regioselectivity and represents a sustainable and economic alternative to those processes based on stoichiometric reagents. Copyright
- Cabrero-Antonino, Jose R.,Leyva-Perez, Antonio,Corma, Avelino
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supporting information; experimental part
p. 678 - 687
(2012/04/18)
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- Microwave-assisted synthesis of disulfides
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A new microwave-assisted synthesis methodology for the preparation of substituted disulfide derivatives is presented. 4-Substituted sulfenimides were reacted with 4-substituted thiols under neat (to right doughy consistency) conditions in chloroform, with both microwave heating and conventional methods. The resulting 4-substituted disulfide derivatives were obtained at higher yields and in shorter reaction times with microwave heating. Their chemistry was confirmed by 1H-NMR, 13C-NMR, infrared (IR), and elemental analysis.
- Kutuk, Halil,Turkoz, Nalan
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experimental part
p. 1515 - 1522
(2011/10/05)
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- A traceless, one-pot preparation of unsymmetric disulfides from symmetric disulfides through a repeated process involving sulfenic acid and thiosulfinate intermediates
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A variable group of unsymmetric disulfides was prepared under mild reaction conditions and in high yields through the reaction of symmetric disulfides with sulfuryl chloride followed by treatment with thiols in the presence of water.
- Han, Minsoo,Lee, Jong Tak,Hahn, Hoh-Gyu
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experimental part
p. 236 - 239
(2011/02/28)
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- Ligand-free palladium-catalyzed C-S coupling reactions using water as solvent and microwaves
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Herein we demonstrate for the first time a rapid and efficient method for the synthesis of aryl sulfides by the direct substitution reaction of aromatic thiols with aryl halides using water as solvent under microwave irradiation. This procedure offers a high yield in shorter reaction time as compared to conventional methods.
- Velmathi, Sivan,Vijayaraghavan, Reena,Amarendar, Ch.,Pal, Ravindra P.,Vinu, Ajayan
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experimental part
p. 2733 - 2736
(2010/12/25)
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- A versatile and convenient preparation of unsymmetrical diaryl disulfides
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We have developed a convenient method for the synthesis of unsymmetrical diaryl disulfides under mild conditions in excellent yields. The described method is based on the straightforward preparation of 5,5-dimethyl-2-thioxo-1,3, 2-dioxaphosphorinane-2-sulfenyl bromide from readily available 5,5-dimethyl-2-sulfanyl-2-thioxo-l,3,2-dioxaphosphorinane or bis(5,5-dimethyl-2-thioxo-l,3,2-dioxaphosphorinan-2-yl) disulfide. The unsymmetrical diaryl disulfides can be obtained from aromatic thiol derivatives bearing electron-withdrawing or electron-donating groups. Thieme Stuttgart.
- Demkowicz, Sebastian,Rachon, Janusz,Witt, Dariusz
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body text
p. 2033 - 2038
(2009/04/03)
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- Phosphine-free cationic rhodium(I) complex-catalyzed disulfide exchange reaction: Convenient synthesis of unsymmetrical disulfides
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A phosphine-free cationic rhodium(I) complex, [Rh(cod)2]BF 4, is an effective catalyst for disulfide exchange reaction of symmetrical disulfides to unsymmetrical disulfides under inert atmosphere. This reaction could be carried out u
- Tanaka, Ken,Ajiki, Kaori
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p. 5677 - 5679
(2007/10/03)
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- Silicon in Organosulfur Chemistry. Part 3. Disulfide-Silyl Sulfide Interchange. A New Aspect of the Thiol-Disulfide Interchange
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Aryl silyl sulfides (2) undergo interchange reactions with disulfides while, under the same reaction conditions, the corresponding alkyl silyl sulfides are unreactive.Furthermore, the reaction of alkyl aryl disulfides with arylthiosilanes shows a peculiar selectivity in that exchange of the arylthio residues only is observed.This reaction, which represents a new aspect of the well known thiol-disulfide interchange, takes place under mild and neutral conditions.A possible rationalization of the mechanism of this new reaction is also proposed.
- Capozzi, Giuseppe,Menichetti, Stefano,Rosi, Alessandro
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p. 2247 - 2251
(2007/10/02)
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- FACILE REDUCTION OF SULFINIC ACID TO DISULFIDE WITH THIOL AND CHLOROTRIMETHYLSILANE
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Sulfinic acids were found to be readily reduced to the corresponding disulfide quantitatively at room temperature upon treatment with a mixture of thiols and chlorotrimethylsilane.
- Oae, Shigeru,Togo, Hideo,Numata, Tatsuo,Fujimori, Ken
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p. 1193 - 1196
(2007/10/02)
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