16601-17-5Relevant academic research and scientific papers
Phthalimide-Carried Disulfur Transfer to Synthesize Unsymmetrical Disulfanes via Copper Catalysis
Zou, Jiaoxia,Chen, Jinhong,Shi, Tao,Hou, Yongsheng,Cao, Fei,Wang, Yongqiang,Wang, Xiaodong,Jia, Zhong,Zhao, Quanyi,Wang, Zhen
, p. 11426 - 11430 (2019/11/21)
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.
Asymmetric kinetic resolution of sulfides for the construction of unsymmetric sulfides and chiral 3,3-disubstituted oxindoles
Wang, Kaiye,Xiang, Yanan,Shi, Zhujun,Wang, Hongyu,Li, Na,Tang, Bo
supporting information, p. 6351 - 6354 (2019/07/10)
A range of 3,3-disubstituted oxindoles accessed using para-quinone methides derived from isatins with thiols were used for the formation of unsymmetrical disulfides, and 3,3-disubstituted oxindoles with a chiral quaternary carbon center and unsymmetric di
A Novel Method for the Direct Synthesis of Symmetrical and Unsymmetrical Sulfides and Disulfides from Aryl Halides and Ethyl Potassium Xanthogenate
Soleiman-Beigi,Arzehgar
supporting information, p. 986 - 992 (2018/02/09)
An efficient and new method for the synthesis of disulfides and sulfides via the reaction of aryl halides with ethyl potassium xanthogenate in the presence of MOF-199 is described. O -Ethyl- S -aryl carbonodithioate has a key role as an intermediate in this procedure; it was converted into symmetrical diaryl disulfides in DMF. Additionally, this could be applied to the synthesis of unsymmetrical aryl alkyl(aryl′) disulfides by the reaction with S -alkyl(aryl) sulfurothioates (Bunte salts) as well as unsymmetrical aryl alkyl(aryl′) sulfides in DMSO.
Aryl-alkyl asymmetric persulfate compound, and synthesis method and application thereof
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Paragraph 0178-0249; 0418-0425, (2017/02/24)
The invention discloses an aryl-alkyl asymmetric persulfate compound shown as a formula (3) and a synthesis method thereof. Arylboronic acid shown as a formula (I) and R2SSCOR3 shown as a formula (2) are used as reaction raw materials; under the effects of metal copper catalysts, reaction is performed to obtain the aryl-alkyl asymmetric persulfate compound. The method has the advantages that the reaction conditions are mild; the raw materials are low in cost and easy to obtain; the reaction operation is simple; the yield is higher; cheap metal is used as catalysts in the reaction process; economy and practicability are realized; the environment-friendly performance is achieved; reaction substrates can be easily prepared; after the reaction amplification, the reaction efficiency is high. The prepared aryl-alkyl asymmetric persulfate compound shown as the formula (3) and prepared by the method can be used for further synthesizing potential medicine compounds containing C-S bonds, such as benzyl (phenyl) thioether and benzyl (4-methoxy phenyl) thioether. The aryl-alkyl asymmetric persulfate compound and the synthesis method provided by the invention have the advantages of wide application prospects and practical value.
Nucleophilic disulfurating reagents for unsymmetrical disulfides construction via copper-catalyzed oxidative cross coupling
Dai, Zhihong,Xiao, Xiao,Jiang, Xuefeng
, p. 3702 - 3706 (2017/06/13)
Novel disulfuration was established via cross coupling between nucleophilic disulfurating reagent and arylsilane introducing two sulfur atoms in one step. This methodology was applied to synthesize various unsymmetrical disulfides under mild conditions via copper-catalyzed oxidative Hiyama-type cross coupling, providing a new pathway for disulfide synthesis. In addition, pH value of system displayed a key role in alcoholysis process.
Aryl-aryl, aryl-alkyl, alkyl-alkyl asymmetric the sulfur compounds and its synthetic method
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Paragraph 0156-0159, (2016/11/17)
The invention discloses a synthesis method of aryl-aryl, aryl-alkyl and alkyl-alkyl asymmetric persulfides as shown in a formula (II) or a formula (IV). According to the synthesis method, with sulfinic acid sodium salt, and halogenated hydrocarbon and Na2S2O3 as reaction materials or Bunte salt as a reaction material instead of the halogenated hydrocarbon and Na2S2O3, the aryl-aryl, aryl-alkyl and alkyl-alkyl asymmetric persulfides are obtained by reaction in the absence of transition metal. The synthesis method has the advantages that the reaction is efficient; the yield is high; a vulcanizing reagent is cheap, easily available, stable, and free of pungent smell; no strong acid or alkali or extra oxidizing or reducing agent is added in reaction; the condition is relatively mild; and no transition metal is used as a catalyst in the reaction, and therefore the method is economical, practical and friendly to the environment; a reaction substrate is easy to prepare; the reaction efficiency is high after the reaction is amplified, and therefore, the synthesis method has a wide application prospect and practical value.
Transition-metal-free persulfuration to construct unsymmetrical disulfides and mechanistic study of the sulfur redox process
Xiao, Xiao,Feng, Minghao,Jiang, Xuefeng
, p. 4208 - 4211 (2015/03/30)
A sulfur redox process has been developed between sulfinate and thiosulfate, which efficiently affords diverse unsymmetrical disulfides and provides a new method to modify pharmaceuticals and natural products without requiring an extra oxidant or reductant. Gram-scale investigation further demonstrates the practicality and application potential of this process. Isolated key intermediates and a series of control experiments afford an unusual process, which reveals the mechanism of comproportionation and the transition-metal-free sulfur redox process.
Cleavage of oxygen-sulfur double bonds and carbon-sulfur bonds: Unusual highly selective electrophilic addition of allenylic sulfoxides
Wang, Minyan,Fu, Chunling,Ma, Shengming
, p. 1016 - 1022 (2013/06/27)
Selective cleavage and formation of covalent bonds is an everlasting topic in the science of synthesis. Recently, much attention has been paid to the activation and functionalization of inert covalent chemical bonds such as C-H, C-O, C-Cl bonds, etc. In this edge article, we report that hydrogen bonding may mediate efficient and highly selective cleavage of OS and C-S bonds in 1,2-allenyl sulfoxides with I2 and BnSH, which transfer the oxygen to the adjacent allenylic carbon atom forming a ketone or aldehyde carbonyl functionality with one CC bond in the allene moiety remaining in a highly stereoselective manner. This method provides a general and highly stereoselective route to the synthetically important yet difficult to prepare polysubstituted enals or enones.
A new electrochemical method of preparation of unsymmetrical disulfides
Do, Quang Tho,Elothmani, Driss,Le Guillanton, Georges,Simonet, Jacques
, p. 3383 - 3384 (2007/10/03)
A new method is described for the preparation of unsymmetrical disulfides by reaction of the electrogenerated sulfenium cation R1-S+ with thiols or disulfides.
OXIDATION OF THIOL WITH 5-ARYLIDENE-1,3-DIMETHYLBARBITURIC ACID: APPLICATION TO SYNTHESIS OF UNSYMMETRICAL DISULFIDE
Tanaka, Kiyoshi,Chen, Xing,Yoneda, Fumio
, p. 3241 - 3250 (2007/10/02)
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.
