18513-19-4Relevant academic research and scientific papers
Method for synthesizing sulfone compounds under photocatalysis condition
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Paragraph 0110-0113, (2021/03/31)
The invention belongs to the technical field of compound preparation, and particularly relates to a method for synthesizing sulfone compounds under a photocatalysis condition. Aromatic hydrazine and sulfinate are used as raw materials, and under the action of alkali and a solvent, a sulfone compound is generated through reaction under the condition of air or oxygen under the illumination of visible light. According to the method disclosed by the invention, aryl hydrazine is used as an arylation reagent, polyacid salt is used as a catalyst or an organic photosensitizer is used as a catalyst, and the sulfones compound can be efficiently synthesized by coupling with sulfinate under the condition of room temperature through visible light irradiation. The method has good substrate universalityand relatively mild reaction conditions, is not only a substitute for synthesizing sulfone compounds by coupling from simple substrates reported at present, but also broadens the new application of the polyacid salt in the field of photocatalysis.
On the important transition of sugar-based surfactant as a microreactor for C-S coupling in water: From micelle to vesicle
Ge, Xin,Lei, Qiuyun,Liao, Xiong,Liu, Xuemin,Song, Weili,Wu, Lei,Wu, Siyuan,Zhou, Shaodong
, (2021/09/15)
A reversible, temperature-induced micelle-to-vesicle transition of a sugar-based pseudogemini surfactant (C11D12) was employed for copper-catalyzed C-S coupling in water. The phase behavior and morphology of the C11D12 aqueous solution were investigated by DLS and cryo-TEM. The aggregates undergo a series of transitions upon increasing the temperature: spherical micelles were initially transformed into large vesicles, but they eventually transformed into smaller vesicles. The vesicular catalytic protocol accommodates an excellent substrate scope with moderate to high yields. The mechanisms of temperature-induced aggregate transition and vesicular catalysis were elucidated by experimental results and DFT calculations. It was revealed that the charge layer of the vesicle grants stronger nucleophilicity to the PhSO2-Cu-D12Ga intermediate. Furthermore, the aqueous reaction medium can be recycled and reused several times after easily separating the precipitated product.
A highly active and easily recoverable chitosan@copper catalyst for the C-S coupling and its application in the synthesis of zolimidine
Shen, Chao,Xu, Jun,Yu, Wenbo,Zhang, Pengfei
supporting information, p. 3007 - 3012 (2014/06/10)
Aryl sulfones were synthesized using a highly active and easily recoverable heterogeneous Cu catalyst which was prepared by simply stirring an aqueous suspension of chitosan in water with copper salts. The chitosan@copper catalyst catalyzed the coupling reactions of aryl halides with sodium sulfinates to readily give the corresponding sulfones in good to excellent yields. The highly active catalyst can be reused many times without losing its catalytic activity. In addition, by using this protocol, the marketed drug zolimidine (antiulcer) could be synthesized easily. This journal is the Partner Organisations 2014.
A mild and efficient synthesis of aryl sulfones from aryl chlorides and sulfinic acid salts using microwave heating
Yuan, Yan-Qin,Guo, Sheng-Rong
supporting information; experimental part, p. 2750 - 2756 (2011/12/04)
The CuCl-catalyzed coupling of aryl chlorides and sulfinic acid salts provides a simple and extremely efficient route to unsymmetrical aryl sulfones in high to excellent yields under microwave irradiation within 3-30 minutes. Georg Thieme Verlag Stuttgart · New York.
General copper-catalyzed transformations of functional groups from arylboronic acids in water
Yang, Haijun,Li, Yong,Jiang, Min,Wang, Junmei,Fu, Hua
experimental part, p. 5652 - 5660 (2011/06/23)
A simple and general copper-catalyzed method has been developed for transformations of various functional groups (i I, i N3, i SO2R, i OH, i NH2, and i NO 2) on aromatic rings from arylboronic acids in water under air. The protocol uses cheap and readily available inorganic salts (KI, NaN3, NaSO2R, NaOH, NaNO2) and aqueous ammonia as the functional-group sources, simple Cu2O/NH3 as the catalyst system, environmentally friendly water as the solvent, and oxygen in air as the oxidant. Importantly, the copper catalyst system in water was recyclable. This study should provide a useful strategy for interconversions of the functional groups on aromatic rings.
Synthetic study of substituted arylsulfonylphenylbenzamides
Gong, Denghuang,Li, Jiafeng,Yuan, Chengye,Yuan, Junying
, p. 55 - 66 (2007/10/03)
For the structure-activity relationship, a series of substituted arylsulfonyl-phenylbenzamides is reported.
Ionic liquid-accelerated arylation of sodium arenesulfinates with diaryliodonium salts used for the synthesis of diaryl sulfones
Wang, Feng-Yan,Chen, Zhen-Chu,Zheng, Qin-Guo
, p. 620 - 621 (2007/10/03)
Arylation of sodium arenesulfinates with diaryliodonium salts can be performed with good yields in the room-temperature ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate ([BMim]BF4), which provides an efficient method for the synthesis of diaryl sulfones; the ionic liquid can be recycled and reused.
Convenient one-pot procedure for converting aryl sulfides to nitroaryl sulfones
Nose, Masatoshi,Suzuki, Hitomi
, p. 1065 - 1071 (2007/10/03)
When treated with nitrogen dioxide and ozone in inert solvent at 0°C or below, aryl sulfides underwent smooth oxidative nitration to give nitroaryl sulfones in good yield. Using this methodology, a series of mono- and di-nitrated aryl sulfones were prepared from methyl phenyl sulfide and diphenyl sulfide and their physical data are presented.
Hypervalent iodine in synthesis 67: A convenient method for the synthesis of diaryl sulfones by palladium-catalysed arylation of sodium arenesulfinates with diaryliodonium salts
Zhou,Chen
, p. 474 - 475 (2007/10/03)
In the presence of Ph(PPh3)4, diaryliodonium salts react with sodium arenesulfinates to produce diaryl sulfones in reasonable yields under mild reaction conditions.
1H and 13C NMR Study of Substituted Effects in 2- and 3-Substituted Diphenyl Sulphides and Sulphones and 4-Substituted 2',6'-Dimethyldiphenyl Sulphides
Perumal, Subbu,Chandrasekaran, Ramasubbu,Vijayabaskar, Veerappan,Wilson, David A.
, p. 779 - 790 (2007/10/03)
The proton and carbon NMR spectra of nine 2-substituted diphenyl sulphides (S-2-X), seven 3-substituted diphenyl sulphides (S-3-X), nine 2-substituted diphenyl sulphones (SO2-2-X), nine 3-substituted diphenyl sulphones (SO2-3-X) and nine 4-substituted-2',6'-dimethyldiphenyl sulphides (Me2-S-4-X) were obtained.Correlations of the 1H and 13C chemical shifts were made with benzene substituent-induced chemical shifts (Lynch plots) and Hammett and dual-substituent parameters and the results were compared with those of 4-substituted diphenyl sulphides (S-4-X) and sulphones (SO2-4-X).The main conclusions are as follows: (i) the transmission of the substituent effects in substituted diphenyl sulphides decreases in the order S-4-X ca.S-2-X > Me2-S-4-X > S-3-X; (ii) the inductive effects are transmitted to a larger extent than the resonance effects to the unsubstituted ring in 3-substituted diphenyl sulphides, while the reverse trend is observed in other substituted diphenyl sulphides; (iii) in 2-methoxy-, 2-chloro-, 2-bromo- and 2-nitrodiphenyl sulphides, an increase in the size of the substituent causes an upfield shift for H-6 ascribable to the repulsion between the lone pairs of electrons on the sulphur and the substituent and its influence on the conformation; (iv) the diminished transmission of substituent effects to the remote rings in 4-substituted 2',6'-dimethyldiphenyl sulphides is probably due to the orthogonal orientation of the rings; and (v) the signal due to the H-6 of 2-substituted diphenyl sulphones suffers a downfield shift with an increase in the size of the substituent, this being ascribable to the increasing steric interaction between the 2-substituent and the sulphonyl oxygen and consequent changes in the conformation. - Keywords: NMR; 1H NMR; 13C NMR; diphenyl sulphides; diphenyl sulphones; ?-polarization
