28856-78-2Relevant academic research and scientific papers
Mechanistic Study of a Photocatalyzed C-S Bond Formation Involving Alkyl/Aryl Thiosulfate
Li, Yiming,Xie, Weisi,Jiang, Xuefeng
, p. 16059 - 16065 (2015)
This study presents thioether construction involving alkyl/aryl thiosulfates and diazonium salt catalyzed by visible-light-excited [Ru(bpy)3Cl2] at room temperature in 44-86 % yield. Electron paramagnetic resonance studies found that thiosulfate radical formation was promoted by K2CO3. Conversely, radicals generated from BnSH or BnSSBn (Bn=benzyl) were clearly suppressed, demonstrating the special property of thiosulfate in this system. Transient absorption spectra confirmed the electron-transfer process between [Ru(bpy)3Cl2] and 4-MeO-phenyl diazonium salt, which occurred with a rate constant of 1.69×109 M-1 s-1. The corresponding radical trapping product was confirmed by X-ray diffraction. The full reaction mechanism was determined together with emission quenching data. Furthermore, this system efficiently avoided the over-oxidation of sulfide caused by H2O in the photoexcited system containing Ru2+. Both aryl and heteroaryl diazonium salts with various electronic properties were investigated for synthetic compatibility. Both alkyl- and aryl-substituted thiosulfates could be used as substrates. Notably, pharmaceutical derivatives afforded late-stage sulfuration smoothly under mild conditions.
Aryl alkyl, aryl aryl thioether compound and its synthesis method
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Paragraph 0127-0130, (2017/08/16)
The invention discloses a synthesis method of an aryl-alkyl and aryl-aryl thioether compound represented by a formula (III). According to the synthesis method, aryl tetrafluoroboric acid diazonium salt is taken as a reaction raw material in a reaction solvent, aryl and alkyl thiosulfate is taken as a sulfurizing agent, and the materials react under the catalysis action of visible light and a photosensitive agent to obtain the aryl-alkyl and aryl-aryl thioether compound. According to the synthesis method, the raw materials are easy to obtain and are cheap, the reaction operation is simple, the reaction condition is mild and environment-friendly, the yield is higher, the functional group tolerance is excellent, later modification of drugs is successfully realized, and an efficient C-S bond construction method is provided for medicinal chemistry and biological orthogonal chemistry research.
Ionic liquid as base and phase transfer agent: A green protocol for the synthesis of diaryl sulphides in water
Kundu, Debasish,Ranu, Brindaban C.
, p. 1761 - 1765 (2014/01/17)
A basic ionic liquid, 1-methyl-3-butylimidazolium hydroxide, [BMIm]OH, acts as a base and phase transfer agent in the copper-catalysed ligand free S-arylation in water. A variety of iodo and bromoaryl compounds undergo coupling with aryl and heteroaryl thiols in presence of this ionic liquid in water to provide the corresponding diaryl/aryl-heteroaryl sulfides. The use of benign [BMIm]OH and water as reaction medium makes this procedure greener and cost effective.
Recyclable heterogeneous supported copper-catalyzed coupling of thiols with aryl halides: base-controlled differential arylthiolation of bromoiodobenzenes
Bhadra, Sukalyan,Sreedhar, Bojja,Ranu, Brindaban C.
experimental part, p. 2369 - 2378 (2009/12/28)
Alumina-supported copper sulfate efficiently catalyzes the 5-arylation of aromatic, heteroaromatic and aliphatic thiols with aryl as well as heteroaryl halides under aerobic, ligand-free conditions. This protocol provides an easy access to a variety of thioethers as well as unsymmetrical bis-thioethers by base-controlled differential coupling of thiols with iodo- and bromo-substituents in an aromatic halide. The catalyst is inexpensive, non-air sensitive, environmentally friendly and recyclable.
