- Transformation of arylboronic acids with sodium thiosulfate into organodisulfides catalyzed by a recyclable polyoxometalate-based Cr(iii) catalyst
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Organo disulfides represent an abundant class of compounds in chemical biology, pharmaceutical fields, and industry. They are traditionally synthesized by the oxidation of mercaptan in the presence of an organic ligand supported metal catalyst or toxic oxidants under harsh conditions. Here, we disclose a highly-efficient pathway in which disulfide is synthesized by organic boric acid and Na2S2O3 using the catalyst (NH4)3[CrMo6O18(OH)6], demonstrating a high activity and excellent selectivity. Various boric acid derivatives have been successfully transformed into the corresponding disulfides. Mechanistic insights have been furnished based on the observation of intermediate and control experiments.
- Chang, Yalin,Li, Huiyi,Tao, Chaofu,Wang, Aiping,Wei, Yongge,Xie, Ya,Yu, Han,Yu, Shunming
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supporting information
p. 6059 - 6064
(2021/08/23)
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- Phthalimide-Carried Disulfur Transfer to Synthesize Unsymmetrical Disulfanes via Copper Catalysis
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A versatile Cu-catalyzed cross-coupling reaction to various unsymmetrical disulfanes has been presented, from phthalimide-carried disulfur transfer reagents and commercially available boronic acids under mild and practical conditions. The method features the unprecedented use of phthalimide-carried disulfurating reagents (Harpp reagent) in cross-coupling chemistry and is highlighted by the broad substrate scopes, even applicable for the transfer of aryl-disulfur moieties (ArSS-). Notably, the robustness of this methodology is shown by the late-stage modification of bioactive scaffolds of coumarin, estrone, and captopril.
- Zou, Jiaoxia,Chen, Jinhong,Shi, Tao,Hou, Yongsheng,Cao, Fei,Wang, Yongqiang,Wang, Xiaodong,Jia, Zhong,Zhao, Quanyi,Wang, Zhen
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p. 11426 - 11430
(2019/11/21)
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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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- 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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- OXIDATION OF THIOL WITH 5-ARYLIDENE-1,3-DIMETHYLBARBITURIC ACID: APPLICATION TO SYNTHESIS OF UNSYMMETRICAL DISULFIDE
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5-Arylidene-1,3-dimethylbarbituric acid derivatives, such as 1a and 1b, effectively oxidized both alkane- and benzenethiols to disulfides under neutral condition with concomitant formation of the dihydro compounds (2a) and (2b).Thiol adduct of the dihydro compound was prepared as a stable compound and successfully applied to the synthesis of unsymmetrical disulfide under mild condition in excellent yield.Mechanistic consideration for the oxidation was also described briefly.
- Tanaka, Kiyoshi,Chen, Xing,Yoneda, Fumio
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p. 3241 - 3250
(2007/10/02)
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- OXIDATION OF THIOL BY 5-ARYLIDENE 1,3-DIMETHYLBARBITURIC ACID AND ITS APPLICATION TO SYNTHESIS OF UNSYMMETRICAL DISULFIDE
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Oxidation of both aromatic and aliphatic thiols by 5-arylidene 1,3-dimethylbarbituric acid was found to proceed readily to give disulfides in good yield with concomitant reduction of the oxidant to the dihydro compound.Thiol adduct of the dihydro compound was succesfully applied to the synthesis of unsymmetrical disulfide under mild conditions in an excellent yield.
- Tanaka, Kiyoshi,Chen, Xing,Kimura, Teiji,Yoneda, Fumio
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p. 4173 - 4176
(2007/10/02)
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- 4'-NITROARENESULPHENANILIDES: THEIR USE IN THE SYNTHESIS OF UNSYMMETRICAL DISULPHIDES
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The reaction of 4'-nitroarenesulphenanilides with thiols in the presence of boron trifluoride etherate can provide an effective route to unsymmetrical disulphides.
- Benati, L.,Montevecchi, P. C.,Spagnolo, P.
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p. 1739 - 1742
(2007/10/02)
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