- Ammonium iodide-mediated electrosynthesis of unsymmetrical thiosulfonates from arenesulfonohydrazides and thiols
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Unsymmetrical thiosulfonates were synthesized from thiols and arenesulfonohydrazides by their electrolysis in undivided cell equipped with graphite anode and stainless steel cathode under high current density applying NH4I both as a redox catal
- Terent'ev, Alexander O.,Mulina, Olga M.,Ilovaisky, Alexey I.,Kokorekin, Vladimir A.,Nikishin, Gennady I.
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- Visible-light-promoted synthesis of secondary and tertiary thiocarbamates from thiosulfonates andN-substituted formamides
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A general visible-light-promoted metal-free synthesis of secondary and tertiary thiocarbamates starting from thiosulfonates andN-substituted formamides is developed. By employing rhodamine B as a photocatalyst andtert-butyl hydroperoxide (TBHP) as an oxidant, a wide scope of thiocarbamates can be obtained through direct thiolation of acyl C-H bonds under irradiation of blue light at room temperature for 12 h.
- Bi, Wen-Zhu,Zhang, Wen-Jie,Li, Zi-Jie,He, Yuan-Hao,Feng, Su-Xiang,Geng, Yang,Chen, Xiao-Lan,Qu, Ling-Bo
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supporting information
p. 8701 - 8705
(2021/10/22)
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- Visible-Light-Induced Radical Cascade Reaction of 1-Allyl-2-ethynylbenzoimidazoles with Thiosulfonates to Assemble Thiosulfonylated Pyrrolo[1,2-a]benzimidazoles
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A visible-light-induced radical domino reaction of 1-allyl-2-ethynylbenzoimidazoles with thiosulfonates was developed, which generated the thiosulfonylated pyrrolo[1,2-a]benzimidazoles in moderate to good yields. This reaction proceeded under transition-metal-free conditions with good functional group tolerance and high regioselectivity. The possible pathway involved thiosulfonates were activated through the energy transfer route promoted by photocatalysis.
- Liu, Yan,Zhang, Niuniu,Xu, Yanli,Chen, Yanyan
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p. 16882 - 16891
(2021/11/18)
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- Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives
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A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, and β-keto thiosulfones, respectively. The nucleophilic addition of two molecular sulfoxonium ylides to construct sulfone-substituted 1,4-dione compounds is the highlight of this work.
- Wang, Fei,Liu, Bo-Xi,Rao, Weidong,Wang, Shun-Yi
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supporting information
p. 6600 - 6604
(2020/09/02)
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- H2O2-mediated metal-free protocol towards unsymmetrical thiosulfonates from sulfonyl hydrazides and disulfides in PEG-400
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A green and practical protocol between sulfonyl hydrazides and disulfides is herein reported for the synthesis of unsymmetrical thiosulfonates with the assistance of H2O2 in PEG-400, releasing N2 and H2O as the byproducts. The efficient and compatible process was considered to take place in the absence of metallic catalysts through a radical mechanism as determined by EPR analysis.
- Peng, Zhihong,Zheng, Xiao,Zhang, Yingjun,An, Delie,Dong, Wanrong
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supporting information
p. 1760 - 1764
(2018/04/30)
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- Copper-Catalyzed TBHP-Mediated Radical Cross-Coupling Reaction of Sulfonylhydrazides with Thiols Leading to Thiosulfonates
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A tert-butyl hydroperoxide (TBHP)-mediated coupling of sulfonylhydrazides with thiols catalyzed by CuBr2 to afford thiosulfonates via a radical process is described.
- Zhang, Guo-Yu,Lv, Shuai-Shuai,Shoberu, Adedamola,Zou, Jian-Ping
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p. 9801 - 9807
(2017/09/22)
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- Facile synthesis of symmetric thiosulfonates by oxidation of disulfide with oxone/MX (MX = KBr, KCl, NaBr and NaCl)
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Abstract A new method is described for the oxidation of aliphatic- and aromatic disulfides containing electron-donating and electron-withdrawing groups to their corresponding thiosulfonates using oxone in combination with the MX (MX = KBr, KCl, NaBr and NaCl). No obvious electronic effects influence the yields of thiosulfonates. Avoiding the usage of toxic and unstable reagents, mild reaction conditions, short reaction times and cost-effectiveness are advantages of this methodology when likened to known methods for thiosulfonates syntheses.
- Natarajan, Palani
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p. 4131 - 4134
(2015/08/03)
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- Sc(OTf)3-catalyzed synthesis of thiosulfonates in ionic liquid-water
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The first example of Sc(OTf)3-catalyzed sulfenylation of sodium sulfinates with N-(organothio)succinimides in ionic liquids (ILs) and water cosolvent system was developed, achieving thiosulfonates in moderate to excellent yields. Additionally, Sc(OTf)3/ILs could be recovered easily after the reactions and reused without a significant loss in the catalytic activity. Thus, the present protocol represents an interesting complement to known methods for thiosulfonates synthesis.
- Liang, Gaigai,Chen, Jing,Chen, Jiali,Li, Wanmei,Chen, Jiuxi,Wu, Huayue
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supporting information
p. 6768 - 6770
(2013/01/15)
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- NBS-promoted sulfenylation of sulfinates with disulfides leading to unsymmetrical or symmetrical thiosulfonates
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A highly practical method to access unsymmetrical and symmetrical thiosulfonates in moderate to excellent yields has been developed through NBS-promoted sulfenylation of sulfinates with disulfides. The present process enables the use of two RS in RSSR and shows broad functional group tolerance, which represents an atom-economical and practical procedure for the synthesis of thiosulfonates. A plausible mechanism for the role of NBS as a promoter for the cleavage of disulfides generating N-(organothio)succinimide that then undergos facile sulenylation with sulfinates is proposed. Copyright
- Liang, Gaigai,Liu, Miaochang,Chen, Jiuxi,Ding, Jinchang,Gao, Wenxia,Wu, Huayue
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experimental part
p. 1611 - 1616
(2012/09/07)
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- Hypervalent iodine in synthesis. XXII: A novel way for the preparation of unsymmetric S-aryl thiosulfonates by the reaction of potassium thiosulfonates with diaryliodonium salts
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Unsymmetric S-aryl thiosulfonates can be generated through a novel way for the reaction of potassium thiosulfonates with diaryliodonium salts in good yields under mild conditions.
- Xia, Min,Chen, Zhen-Chu
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p. 1309 - 1313
(2007/10/03)
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