20333-41-9Relevant articles and documents
Simple conversion of thiols to disulfides in EtOH under ambient aerobic conditions without using any catalyst or additive
Wang, Hang,Huang, Guojun,Sun, Yang,Liu, Yunyun
, p. 96 - 97 (2014)
EtOH was found to be an excellent medium for the aerobic S-S coupling reactions of various alkyl and aryl thiols. A series of useful disulfides RSSR have been synthesised in good to excellent yields without using any additional catalyst, oxidant or additive. Moreover, most products could be obtained by simply removing the solvent after completion of the reaction. Satisfactory results were obtained for both mg- and g-scale reactions.
Highly efficient oxidative coupling of thiols by active manganese dioxide (AMD) and barium manganate (BM) under solvent-free conditions at room temperature
Firouzabadi,Abbassi,Karimi
, p. 2527 - 2531 (1999)
Active manganese dioxide (AMD) and commercially available barium manganate (BM) are highly efficient oxidizing agents for oxidative coupling of thiols to their corresponding disulfides in excellent yields under solvent-free conditions at room temperature.
γ-PCC and γ-PCC-SiO2 as efficient reagents for oxidation of thiols to disulfides
Khodaei, Mohammad Mehdi,Salehi, Peyman,Goodarzi, Maryam,Yazdanipour, Ateesa
, p. 3661 - 3666 (2004)
Oxidative coupling of thiols to the corresponding symmetrical disulfides was performed in the presence of γ-picolinium chlorochromate and its silica gel supported. The reactivity of silica gel supported γ-picolinium chlorochromate for thiophenol derivativ
Metal-free chalcogenation of cycloketone oxime esters with dichalcogenides
Ji, Liangshuo,Qiao, Jiamin,Liu, Junjie,Tian, Miaomiao,Lu, Kui,Zhao, Xia
supporting information, (2021/06/15)
We report the metal-free chalcogenation of cycloketone oxime esters with dichalcogenides via a radical process. Because of the metal-free condition and use of readily accessible dichalcogenides, this method is an effective and green strategy for the synthesis of chalcogen-substituted butyronitrile.
Copper-catalyzedortho-selective direct sulfenylation ofN-aryl-7-azaindoles with disulfides
Ru-Jian, Yu,Chun-Yan, Zhang,Xiang, Zhou,Xiong, Yan-Shi,Duan, Xue-Min
supporting information, p. 2901 - 2906 (2021/04/14)
A copper-catalyzed direct C-H chalcogenation ofN-aryl-azaindoles with disulfides is described. This transformation was performed using Earth abundant Cu(OAc)2as a catalyst, benzoic acid as an additive, air as a terminal oxidant, and readily available diaryl and dialkyldisulfides (or diselenide) as chalcogenation reagents. High functional group tolerance and excellent regioselectivity are demonstrated by the efficient preparation of a wide range ofortho-sulfenylation-7-azaindoles.
Transformation of arylboronic acids with sodium thiosulfate into organodisulfides catalyzed by a recyclable polyoxometalate-based Cr(iii) catalyst
Chang, Yalin,Li, Huiyi,Tao, Chaofu,Wang, Aiping,Wei, Yongge,Xie, Ya,Yu, Han,Yu, Shunming
supporting information, p. 6059 - 6064 (2021/08/23)
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.
Palladium-Catalyzed Picolinamide-Directed Benzylic C(sp3)?H Chalcogenation with Diaryl Disulfides and Diphenyl Diselenide
Wang, Kai,Hou, Jiahao,Zhang, Changjun,Cheng, Ke,Bai, Renren,Xie, Yuanyuan
supporting information, p. 2947 - 2952 (2020/06/17)
The first palladium-catalyzed direct benzylic C(sp3)?H chalcogenation with diaryl disulfides and diphenyl diselenide has been established. The coupling reaction proceeds between the thioether radical and palladiumcycle intermediate. Picolinamide serves as an excellent directing group for the C?H activation of benzylic C(sp3)?H and can be easily removed. The current protocol exhibits a relatively broad substrate scope and high functional group compatibility. A mechanistic study indicates that palladium(IV) intermediate is probably formed during the course of the reaction. (Figure presented.).
Extended Pummerer fragmentation mediated by carbon dioxide and cyanide
Liu, Jian,Kragh, Rasmus R.,Kamounah, Fadhil S.,Lee, Ji-Woong
, (2020/10/30)
Pummerer rearrangement reactions generate sulfur (II) oxidation state from sulfur (IV) starting materials in the presence of activating reagents. We found unprecedented transformation of vinyl sulfoxide; disulfide formation reactions mediated by atmospheric pressure of carbon dioxide in extended Pummerer rearrangement reactions. Only under CO2 atmosphere, we observed moderate to high yields of disulfide starting from sulfur (IV) starting materials. Investigations on the reaction mechanism revealed that the degradation of the starting materials and the products was significant in the absence of CO2. Further evidence for the suggested reaction mechanism was obtained by a cross-over experiment and a radical trapping reagent.
Natural gallic acid catalyzed aerobic oxidative coupling with the assistance of MnCO3 for synthesis of disulfanes in water
Song, Lijuan,Li, Wenhao,Duan, Wenxue,An, Jichao,Tang, Shanyu,Li, Longjia,Yang, Guanyu
supporting information, p. 1432 - 1438 (2019/03/26)
The formation of S-S bonds has great significance and value in synthetic chemistry and bioscience. To pursue a sustainable approach for such a synthesis, an aerobic oxidative coupling method for the efficient preparation of organic disulfanes, using a low-toxic natural gallic acid as an organocatalyst, inexpensive MnCO3 as a cocatalyst, O2 as the terminal oxidant and water as the solvent, has been successfully developed. Such metal-organic cooperative catalytic protocol provided an access to various symmetrical and unsymmetrical disulfanes in up to 99% yield. Gram scale synthesis with practical convenience and low loading of catalysts further illustrates the practicability of our method.
Palladium(II)/Copper(II)-Catalyzed C–H Sulfidation or Selenation of Arenes Leading to Unsymmetrical Sulfides and Selenides
Nishino, Kota,Tsukahara, Shouya,Ogiwara, Yohei,Sakai, Norio
supporting information, p. 1588 - 1593 (2019/02/09)
A novel palladium(II)/copper(II)-catalyzed sulfidation of the C–H bond in electron-rich arenes and in pentafluorobenzene with disulfides was developed. This catalytic system can be used to efficiently produce various types of either unsymmetrical aryl sulfides or alkyl aryl sulfides. The present protocol could also be applied to the direct preparation of unsymmetrical aryl selenides via C–H selenation.
