- Preparation method of thiosulfonate compound
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The invention belongs to the field of organic synthetic chemistry, and particularly discloses a preparation method of a thiosulfonate compound. The specific preparation process comprises the following steps: taking aryl diazonium salt, sodium pyrosulfite and thiophenol/mercaptan as raw materials, taking organic dye as a photocatalyst, adding an organic solvent, and reacting for 12 hours at room temperature under the irradiation of an LED visible light lamp and nitrogen protection to generate thiosulfonate; and after the reaction is finished, adding distilled water into the reaction system, extracting the reaction liquid with ethyl acetate, concentrating the extraction liquid to obtain a crude product, and carrying out silica gel column chromatography separation on the crude product to obtain thiosulfonate. According to the method, simple and easily available sodium pyrosulfite is used as a sulfone source, cheap organic dye is used as a photocatalyst, clean light energy is used as a reaction energy source, a high-energy-consumption heating device and a metal catalyst or strong acid are not used, the reaction condition is mild, the operation is simple and convenient, and a green synthesis strategy is provided for thiosulfonate.
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Paragraph 0016; 0131-0135
(2021/05/19)
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- Visible-Light-Induced Cyclization/Aromatization of 2-Vinyloxy Arylalkynes: Synthesis of Thio-Substituted Dibenzofuran Derivatives
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A visible-light-induced cascade reaction of 2-vinyloxy arylalkynes with thiosulfonates was developed and provided unexpected thio-substituted dibenzofuran derivatives in moderate yields. Mechanistic studies revealed the thiosulfonylation product of 2-vinyloxy arylalkyne was the key intermediate, and the additive disulfide played the role of hydrogen abstraction in the aromatization process to offer the desired product. This reaction presents a new reaction mode for the construction of polycyclic oxygen heterocycles.
- Chen, Hui,Chen, Yanyan,Mo, Zuyu,Xu, Yanli,Yan, Yunyun,Zhang, Niuniu
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supporting information
p. 376 - 381
(2021/01/13)
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- The organocatalytic synthesis of perfluorophenylsulfides: Via the thiolation of trimethyl(perfluorophenyl)silanes and thiosulfonates
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The organic superbase t-Bu-P4-catalyzed direct thiolation of trimethyl(perfluorophenyl)silanes and thiosulfonates was developed. Yields of perfluorophenylsulfides of up to 97% under catalysis of 5 mol% t-Bu-P4 were achieved. This method was shown to provide an efficient way to construct the perfluorophenyl-sulfur bond under mild metal-free reaction conditions. This journal is
- Cai, Zhihua,Du, Guangfen,He, Lin,Lin, Muze,Luo, Jinyun,Wu, Leifang
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supporting information
p. 9237 - 9241
(2021/11/13)
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- Visible-light induced decarboxylative coupling of redox-active esters with disulfides to construct C-S bonds
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A novel method has been established for the construction of C-S bonds using redox-active esters with disulfides in the presence of Ru-photoredox catalyst. This method exhibits remarkable functional group tolerance across a wide scope of substrates. Under
- Xiao, Zhiwei,Wang, Lu,Wei, Junjie,Ran, Chongzhao,Liang, Steven H.,Shang, Jingjie,Chen, Guang-Ying,Zheng, Chao
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supporting information
p. 4164 - 4167
(2020/04/22)
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- Nickel-Catalyzed Defluorinative Reductive Cross-Coupling Reaction of gem-Difluoroalkenes with Thiosulfonate or Selenium Sulfonate
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A nickel-catalyzed defluorinative reductive cross-coupling of gem-difluoroalkenes with thiosulfonate or selenosulfonates is described. The reaction involves the formation of thiolated or selenylated monofluoroolefins via regioselective C-F bond cleavage and C-S or C-Se bond formation and features easily available substrates, mild reaction conditions, and high E-selectivity. One of the derivatives by further cross coupling with PhMgBr exhibited an aggregation-induced emission enhancement effect.
- Li, Jian,Rao, Weidong,Wang, Shun-Yi,Ji, Shun-Jun
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p. 11542 - 11552
(2019/09/30)
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- Metal-Free Synthesis of Thiosulfonates via Insertion of Sulfur Dioxide
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A simple and catalyst-free strategy was developed for the synthesis of unsymmetrical thiosulfonates using readily available DABCO?(SO2)2 as a solid and bench-stable sulfur dioxide surrogate. The corresponding thiosulfonates were obtained through a radical pathway with good functional group tolerance. This strategy offers a promising synthesis method for the construction of diverse and useful thiosulfonates in the field of synthetic and pharmaceutical chemistry and extends the number of still limited sulfur dioxide fixation strategies. (Figure presented.).
- Li, Guoqing,Gan, Ziyu,Kong, Kexin,Dou, Xiaomeng,Yang, Daoshan
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supporting information
p. 1808 - 1814
(2019/03/28)
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- Method for synthesizing thiosulfonate compounds on the basis of strategy of SO2 insertion
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The invention relates to a method for synthesizing thiosulfonate compounds on the basis of strategy of SO2 insertion. The method includes: performing a reaction in the presence of nitrogen gas and atcertain temperature to prepare the thiosulfonate compoun
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Paragraph 0049; 0050; 0051; 0052; 0053
(2019/04/26)
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- PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes
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A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral pool. The user friendly “trio” enables easy generation of these versatile sulfur analogues and the reaction condition employed depict an economic outline.
- Sarkar, Debayan,Ghosh, Manoj Kumar,Rout, Nilendri
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p. 2360 - 2364
(2018/05/24)
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- Synthesis method of thiosulfonate compound
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The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method of a thiosulfonate compound. The invention provides the synthesis method of the thiosulfonate compound. The method comprises the following steps that methanesulfonohydrazide compounds, thiophenol compounds, oxidizing agents and catalysts are dissolved into a solvent for reaction; purification isperformed to obtain the thiosulfonate compound; oxidizing agents are any one kind or several kinds of materials from tertiary butanol peroxide and catalysts are sodium iodide, potassium iodide, ammonium iodide, iodine element and tetrabutylammonium iodide. Through experiment testing, the thiosulfonate compound prepared by the technical scheme provided by the invention has the advantages that no side reaction occurs; the yield can reach 84 to 100 percent; the conversion rate is high; meanwhile, the used catalysts and catalysts are environment-friendly compounds; the environment pollution cannot be caused; the reaction temperature is low; the method is suitable for industrial mass popularization. The defects that in the prior art, the damage to the environment in the asymmetric thiosulfonates synthesis process is great, and the application to industrial production cannot be realized are overcome.
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Paragraph 0100; 0101; 0102; 0103; 0104; 0106
(2018/07/30)
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- Metal-free NaI/TBHP-mediated sulfonylation of thiols with sulfonyl hydrazides
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A highly efficient sulfonylation of thiols has been achieved through the metal-free NaI/TBHP-mediated cross-coupling of sulfonyl hydrazides and thiols at room temperature. This method provides a convenient and practical route to thiosulfonates in 84-99% y
- Chen, Qian,Huang, Yulin,Wang, Xiaofeng,Wu, Jiawei,Yu, Guodian
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p. 1713 - 1719
(2018/03/21)
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- Electrochemical sulfonylation of thiols with sulfonyl hydrazides: A metal- and oxidant-free protocol for the synthesis of thiosulfonates
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An efficient electrochemical transformation of structurally diverse sulfonyl hydrazides and thiols into thiosulfonates in the presence of ammonium iodide as redox catalyst and electrolyte in acetonitrile at ambient temperature is reported. Transition metal- and oxidant-free conditions are the striking features of this protocol. The in vitro cytotoxicity of all compounds is evaluated by MTT assay against four human cancer cell lines. The results reveal that 3ac and 3ag exhibit potential inhibitory activity against tumor cells. Furthermore, 3ag inhibits cell migration ability and tubulin polymerization in T-24 cells, leading to cell cycle arrest and apoptosis.
- Mo, Zu-Yu,Swaroop, Toreshettahally R.,Tong, Wei,Zhang, Yu-Zhen,Tang, Hai-Tao,Pan, Ying-Ming,Sun, Hong-Bin,Chen, Zhen-Feng
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supporting information
p. 4428 - 4432
(2018/10/17)
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- Visible-light-induced thiotrifluoromethylation of terminal alkenes with sodium triflinate and benzenesulfonothioates
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An unconventional reductive quenching cycle was developed to realize the visible-light-induced thiotrifluoromethylation of terminal alkenes. CF3SO2Na was used as an easy to handle CF3 radical source to afford the desired products in moderate to good yields. Mild reaction conditions and a broad substrate scope feature in this transformation.
- Kong, Weiguang,An, Hejun,Song, Qiuling
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supporting information
p. 8968 - 8971
(2017/08/15)
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