- Photochemical metal-free aerobic oxidation of thiols to disulfides
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Thiol oxidation to disulfides is an area of great importance in organic synthesis, both for synthetic and biological purposes. Herein, we report a mild, inexpensive and green photochemical approach for the synthesis of both symmetrical and non-symmetrical disulfides, using metal-free and environmentally friendly conditions. Utilizing phenylglyoxylic acid as the photoinitiator, common household bulbs as the light source and a simple inorganic salt as the additive, a versatile oxidation of thiols leading to products in excellent yields is described. This journal is
- Spiliopoulou, Nikoleta,Kokotos, Christoforos G.
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supporting information
p. 546 - 551
(2021/01/28)
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- METHOD FOR PRODUCING AROMATIC COMPOUND
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PROBLEM TO BE SOLVED: To provide a BTBT ring (or DNTT ring) construction method in which the reaction proceeds under the atmosphere and at low temperatures (200°C or lower) without separately adding a sulfur source substance as a raw material and without
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Paragraph 0049
(2020/02/06)
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- Thermal conversion of primary alcohols to disulfides: Via xanthate intermediates: An extension to the Chugaev elimination
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Primary alcohols are converted into dialkyl disulfides via heating in situ generated O-alkyl S-difluoro(ethoxycarbonyl)methyl xanthates from ethyl bromodifluoroacetate and potassium xanthates, prepared from primary alcohols and carbon disulfide in the presence of KOH. The reaction mechanism is suggested as an alkyl C[1,3] shift followed by a radical mechanism. This extends to the Chugaev elimination which yields olefins. The current research provides easy access to dialkyl disulfides from commercially available primary alkanols.
- He, Wei,Ding, Yong,Tu, Jianzhuo,Que, Chuqiang,Yang, Zhanhui,Xu, Jiaxi
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p. 1659 - 1666
(2018/03/21)
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- Base-controlled Fe(Pc)-catalyzed aerobic oxidation of thiols for the synthesis of S-S and S-P(O) bonds
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Fe(Pc)-Catalyzed aerobic oxidation of thiols for the synthesis of disulfides has been developed under mild reaction conditions. In addition, an aerobic oxidative cross-dehydrogenative coupling (CDC) reaction of thiols with P(O)-H compounds (H-phosphonates and H-phosphine oxide) for the formation of S-P(O) bonds has been demonstrated under the Fe(Pc) catalysis system with a base additive. Control experiments revealed that the use of a base (DIPA) in this system controls the synthetic pathways in which thiophosphates are formed.
- Huang, Hai,Ash, Jeffrey,Kang, Jun Yong
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p. 4236 - 4242
(2018/06/21)
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- Europhtal (8020) efficiently catalyzes the aerobic oxidation of in situ generated thiols to symmetric disulfides (disulfanes)
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Efficient, odorless and scalable synthetic protocols have been introduced for the preparation of symmetric alkyl disulfides by treatment of the corresponding organic halides with thiourea and NaHCO3in the presence of commercially available Europhtal catalyst (8020) in both H2O and poly ethylene glycol (PEG-200) media at 80–90 °C. Structurally diverse primary, secondary, allylic and benzylic halides were examined successfully whereas, the result with tert-butyl bromide was not satisfactory. Also, another procedure has been introduced for achieving symmetric aryl disulfides in high yields by reacting aryl halides, thiourea and NaHCO3in PEG-200 at 115–120 °C using CuI along with Europhtal catalysts. The results showed that the aerobic oxidation of in situ generated thiols proceeded efficiently in the presence of Europhtal catalyst giving the symmetric disulfide without contamination by symmetric sulfide side-product.
- Abbasi, Mohammad,Sabet, Askar,Sabet, Askar
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- Conversion of organic halides to disulfanes using KCN and CS2
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A sulfur transfer reagent was produced in situ upon stirring a mixture of KCN and CS2 in DMF at r.t. for 15 min, which after heating with an alkyl halide or aryl halide and CuI gave the corresponding symmetric dialkyl or diaryl disulfide, respectively, in high to excellent yields.
- Abbasi, Mohammad,Nowrouzi, Najmeh,Borazjani, Saeedeh Ghassab
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p. 4251 - 4254
(2017/10/11)
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- Synthesis of Disulfanes from Organic Thiocyanates Mediated by Sodium in Silica Gel
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We report an efficient procedure for the synthesis of symmetrical disulfanes from organic thiocyanates in the presence of sodium in silica gel at room temperature. By avoiding the use of foul-smelling thiols, the present protocol provides an attractive alternative to existing methods for the preparation of symmetrical disulfanes.
- Maurya, Chandra Kant,Mazumder, Avik,Kumar, Ajeet,Gupta, Pradeep Kumar
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p. 409 - 411
(2016/02/09)
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- The synthesis of symmetrical disulfides by reacting organic halides with Na2S2O3·5H2O in DMSO
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A one-pot, and scalable method to prepare symmetric disulfides from their corresponding primary, secondary, allylic, and benzylic halides has been developed. In this method, a disulfide is synthesized by reacting an alkyl halide with Na2S2O3·5H2O at 60-70 °C in DMSO.
- Abbasi, Mohammad,Mohammadizadeh, Mohammad Reza,Saeedi, Narges
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supporting information
p. 89 - 92
(2016/01/12)
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- One-pot synthesis of organic disulfides (disulfanes) from alkyl halides using sodium sulfide trihydrate and hexachloroethane or carbon tetrachloride in the poly(ethylene glycol) (PEG-200)
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Abstract Symmetric disulfides are produced by treating their corresponding organic halides including benzylic, allylic, primary and secondary halides with Na2S·3H2O and C2Cl6 or CCl4 in PEG-200 at room temperature in high yields.
- Abbasi, Mohammad,Mohammadizadeh, Mohammad Reza,Moosavi, Hekmat,Saeedi, Narges
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p. 1185 - 1190
(2015/03/31)
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- An efficient metal-free synthesis of organic disulfides from thiocyanates using poly-ionic resin hydroxide in aqueous medium
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An efficient and metal-free method is described for the preparation of organic disulfides from alkyl and acyl methyl thiocyanates in the presence of poly-ionic resin hydroxide in aqueous medium. Further extension of this protocol has been tested using two different organyl thiocyanates to prepare unsymmetrical disulfides.
- Sengupta, Debasish,Basu, Basudeb
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supporting information
p. 2277 - 2281
(2013/05/08)
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- Synthesis, spectral characterization, and crystal structure of two polymorphs of o,o'-dichloro dibenzyl disulfide
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2-Chlorophenyl methanethiol undergoes air oxidation catalyzed by different selenides and yields the corresponding disulfide 1 in two polymorphic forms, 1a and 1b. In the molecular structures of the two new polymorphs of o,o-dichloro dibenzyl disulfide, th
- Srivastava,Rastogi, Rupali,Rajaram,Butcher,Jasinski, Jerry P.
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experimental part
p. 455 - 462
(2010/06/19)
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- An approach to disulfide synthesis promoted by sulfonyl chloride in sodium bicarbonate aqueous media
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A mild and efficient protocol for the synthesis of disulfides in aqueous media using mercaptans promoted by sulfonyl chloride is reported. This reaction offers the advantages of mild reaction conditions, short reaction time, high yields, and simple operation. Taylor & Francis Group, LLC.
- Xiao, Huilong,Chen, Jiuxi,Liu, Miaochang,Wu, Huayue,Ding, Jinchang
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experimental part
p. 2553 - 2559
(2010/03/31)
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- In Search of New Sulfur Transfer Agents
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The chemistry of various sulfur-transfer agents is studied.The reaction of aromatic sulfenyl chloride 5 in the presence of imidazole and/or triethylamine gives the aryl disulfides 7 in 14-85 percent yield, whereas in the case of the corresponding benzylsulfenyl chlorides 9 in the presence of triethylamine and/or caprolactam, both disulfide 10 and benzyl chlorides 11 are formed in 0-81 precent and 10-72 precent yield, respectively. - The transfer reactions of 3-sulfenylated hydantoins 18 with amines are useful for the preparation of the unsymmetric sulfenamides 20 in 31 -61 percent yield.Analogous transfer reactions of compounds 23 and 24 with piperidine give N,N'-thiodipiperidine (3, X = CH2) in 71-80 percent.
- Sosnovsky, George,Krogh, James A.
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p. 121 - 136
(2007/10/02)
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