71732-59-7Relevant academic research and scientific papers
Electrochemical cross-coupling reactions of sodium arenesulfinates with thiophenols and phenols
Ma, Jinfeng,Xu, Pan,Zhong, Zijian,Zhou, Aihua
supporting information, (2021/10/26)
A green electrochemical oxidative cross-coupling protocol for the generation of thiosulfonates and sulfonate esters using sodium arenesulfinates and thiophenols/phenols is disclosed. The protocol involves using inorganic and non-toxic NaI as both redox catalyst and supporting electrolyte at room temperature without oxidant and base. The reactions provide good yields of products and tolerate broad substrate scope. The mechanistic studies revealed that the reactions proceed via a radical pathway for the formation of SO2–S and SO2–O bonds.
Atom transfer radical addition to styrenes with thiosulfonates enabled by synergetic copper/photoredox catalysis
Zhou, Xin,Peng, Zhiyuan,Wang, Peng George,Liu, Qingchao,Jia, Tiezheng
supporting information, p. 1054 - 1059 (2021/02/01)
A synergetic copper/photoredox catalyzed ATRA of styrenes and thiosulfonates is developed. Besides aryl ethylenes, the challenging α-substituted styrenes were employed to construct the benzylic quaternary carbon centers. Owing to the mild conditions as well as the high level of substrate compability, this ATRA could be applied to derivatize bioactive natural products in late stage, and to install fluorophores across alkenes. The mechanistic studies reveal sulfonyl radicals as the key intermediate in the transformation.
Preparation method of thiosulfonate compound
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Paragraph 0016; 0091-0095, (2021/05/19)
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.
TFA promoted multi-component reaction of aryldiazonium with sodium metabisulphite and thiols: Construction of thiosulfonate under transition-metal free conditions
Huang, Cheng-Mi,Li, Jian,Wang, Shun-Yi,Ji, Shun-Jun
supporting information, p. 1923 - 1926 (2020/01/13)
A TFA promoted multi-component reaction of aryldiazonium with sodium metabisulphite and thiols to construct thiosulfonates under transition-metal free conditions is reported. The thiosulfonates were isolated in good yields with broad tolerance of function
Metal-free NaI/TBHP-mediated sulfonylation of thiols with sulfonyl hydrazides
Chen, Qian,Huang, Yulin,Wang, Xiaofeng,Wu, Jiawei,Yu, Guodian
, p. 1713 - 1719 (2018/03/21)
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
Electrochemical sulfonylation of thiols with sulfonyl hydrazides: A metal- and oxidant-free protocol for the synthesis of thiosulfonates
Mo, Zu-Yu,Swaroop, Toreshettahally R.,Tong, Wei,Zhang, Yu-Zhen,Tang, Hai-Tao,Pan, Ying-Ming,Sun, Hong-Bin,Chen, Zhen-Feng
supporting information, p. 4428 - 4432 (2018/10/17)
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.
Oxidative coupling of dichalcogenides with sodium sulfinates via copper-catalyzed cleavage of s-s and se-se bonds
Taniguchi, Nobukazu
, p. 1764 - 1770 (2015/02/19)
A copper-catalyzed sulfonylation of disulfides was achieved using sodium sulfinates in air. The reaction formed various sulfur-sulfone bonds efficiently and afforded thiosulfonates in good yields. Selenosulfonates could also be prepared with this procedure. Furthermore, both chalcogenide groups on the dichalcogenides were available in these reactions.
Copper-catalyzed synthesis of thiosulfonates by oxidative coupling of thiols with sodium sulfinates
Taniguchi, Nobukazu
supporting information, p. 5691 - 5694 (2014/11/07)
The copper-catalyzed sulfonylation of thiols was performed by using sodium sulfinates under an oxygen atmosphere. The procedure afforded thiosulfonates in good yields by using a CuI-Phen?H2O (Phen = 1,10-phenanthroline) catalyst and tolerated numerous combinations of arene- and alkanethiols with sodium sulfinates. Furthermore, it was found that the coupling of diaryl disulfides with sodium arylsulfinates proceeded in air and both sulfide groups on the disulfide were available.
NBS-promoted sulfenylation of sulfinates with disulfides leading to unsymmetrical or symmetrical thiosulfonates
Liang, Gaigai,Liu, Miaochang,Chen, Jiuxi,Ding, Jinchang,Gao, Wenxia,Wu, Huayue
experimental part, p. 1611 - 1616 (2012/09/07)
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
New and facile synthesis of thiosulfonates from sulfinate/disulfide/I2 system
Fujiki, Kiyoko,Tanifuji, Naoki,Sasaki, Yohei,Yokoyama, Taku
, p. 343 - 348 (2007/10/03)
Thiosulfonates were prepared by the iodine oxidative sulfenylation of sulfinates with various disulfides in good yields both in the presence and absence of solvent. One of the important biological applications of sulfenylation is the reaction of cyclic disulfides.
