1512864-83-3Relevant academic research and scientific papers
Copper-Catalyzed Heck-Type Couplings of Sulfonyl Chlorides with Olefins: Efficient and Rapid Access to Vinyl Sulfones
Chen, Qiulin,Liu, Lixia,Wang, Chengming,Xue, Pan
supporting information, (2021/08/27)
A copper-catalyzed redox-neutral alkene sulfonylation reaction has been developed. This reported protocol can be easily scale up to a gram scale, and smoothly applied to the late-stage modification of several bioactive molecules.
Generation of potent Nrf2 activators via tuning the electrophilicity and steric hindrance of vinyl sulfones for neuroprotection
Song, Zi-Long,Hou, Yanan,Bai, Feifei,Fang, Jianguo
, (2020/12/21)
Oxidative stress is constantly involved in the etiopathogenesis of an ever-widening range of neurodegenerative diseases. As a consequence, effective repression of cellular oxidative stress to a redox homeostatic condition is a promising and feasible strategy to treat, or at least retard the progression of, such disorders. Nrf2, a primary orchestrator of cellular antioxidant response machine, is responsible for detoxifying and compensating for deleterious oxidative stress via transcriptional activation of a diverse array of antioxidant biomolecules. In the framework of our persistent interest in disclosing small molecules that interfere with cellular redox-regulating machinery, we report herein the synthesis, optimization, and biological assessment of 47 vinyl sulfone scaffold-bearing small molecules, most of which exhibit robust neuroprotective effect against H2O2-mediated lesions to PC12 cells. After initial screening, the most potent neuroprotective compounds 9b and 9c with marginal cytotoxicity were selected for the follow-up studies. Our results demonstrate that their neuroprotective effects are attributed to the up-regulation of a panel of antioxidant genes and corresponding gene products. Further mechanistic studies indicate that Nrf2 is indispensable for the cellular performances of 9b and 9c, arising from the fact that silence of Nrf2 gene drastically nullifies their protective action. Taken together, 9b and 9c discovered in this work merit further development as neuroprotective candidates for the treatment of oxidative stress-mediated pathological conditions.
Electrochemical Synthesis of Vinyl Sulfones by Sulfonylation of Styrenes with a Catalytic Amount of Potassium Iodide
Wang, Pei-Long,Gao, Hui,Jiang, Zhi-Sheng,Li, Chao,Tian, Zhi-Ao,Li, Pin-Hua
supporting information, p. 1720 - 1724 (2020/09/21)
An electrochemical sulfonylation reaction of styrenes was developed in which sodium arylsulfinates were used as sulfonylating reagents, a catalytic amount of KI was used as a redox mediator, and Bu 4NBF 4was used as the electrolyte. In addition to various styrenes, sodium arylsulfinates with either electron-donating or electron-withdrawing groups were tolerated.
Electrochemical sulfonylation of alkenes with sulfonyl hydrazides: A metal- And oxidant-free protocol for the synthesis of (: E)-vinyl sulfones in water
Cai, Jianpeng,Guo, Huishi,Lai, Yin-Long,Liao, Jianhua,Luo, Jianmin,Mo, Yunyan,Yan, Shaoxi,Zhang, Shengling,Zhu, Lejie
, p. 33155 - 33160 (2020/10/05)
An efficient electrochemical transformation of a variety of alkenes and sulfonyl hydrazides into vinyl sulfones with a catalytic amount of tetrabutylammonium iodide in water is reported. The reaction proceeds smoothly to afford vinyl sulfones with good selectivities and yields at room temperature under air in an undivided cell. Cyclic voltammograms and control experiments have been performed to provide preliminary insight into the reaction mechanism. The key features of this reaction include using pure water as solvent, transition metal- and oxidant-free conditions, and being easily scaled up to gram-scale synthesis. This journal is
Electron Donor-Acceptor Complex Enabled Decarboxylative Sulfonylation of Cinnamic Acids under Visible-Light Irradiation
Ge, Qian-Qian,Qian, Jia-Sheng,Xuan, Jun
, p. 8691 - 8701 (2019/08/30)
Visible-light-induced decarboxylative sulfonylation of cinnamic acids with aryl sulfonate phenol esters enabled by the electron donor-acceptor complex is developed. The method offers a mild and green approach for the synthesis of vinyl sulfones with excellent functional group compatibility under photocatalyst and oxidant-free conditions.
Cross-Coupling of Sodium Sulfinates with Aryl, Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis
Yue, Huifeng,Zhu, Chen,Rueping, Magnus
supporting information, p. 1371 - 1375 (2018/01/27)
An efficient photoredox/nickel catalyzed sulfonylation reaction of aryl, heteroaryl, and vinyl halides has been achieved for the first time. This newly developed sulfonylation protocol provides a versatile method for the synthesis of diverse aromatic sulfones at room temperature and shows excellent functional group tolerance. The electrophilic coupling partners are not limited to aryl, heteroaryl, and vinyl bromides and iodides, but also includes less reactive aryl chlorides as suitable substrates for this transformation.
Electrochemical Decarboxylative Sulfonylation of Cinnamic Acids with Aromatic Sulfonylhydrazides to Vinyl Sulfones
Zhao, Yu,Lai, Yin-Long,Du, Ke-Si,Lin, Dian-Zhao,Huang, Jing-Mei
, p. 9655 - 9661 (2017/09/23)
A stereoselective synthesis of (E)-vinyl sulfones has been developed via electrochemical oxidative N-S bond cleavage of aromatic sulfonylhydrazides, followed by cross-coupling reactions with cinnamic acids to form the C-S bond. The protocol proceeded smoo
PhI(OAc)2-mediated decomposition of N-arylsulfonyl hydrazones: metal-free synthesis of (E)-vinyl sulfones
Luo, Zaigang,Fang, Yuyu,Zhao, Yu,Xu, Xuemei,Feng, Chengtao,Li, Zhong,Zhang, Xiaomei,He, Jie
supporting information, p. 4105 - 4108 (2016/08/18)
A novel and efficient approach for the preparing of (E)-vinyl sulfones via PhI(OAc)2-mediated decomposition of ketone-derived N-arylsulfonyl hydrazones has been developed. The generation of α- or β-substituted vinyl sulfones was affected by the
Iron/copper Co-catalyzed synthesis of vinyl sulfones from sulfonyl hydrazides and alkyne derivatives
Rong, Guangwei,Mao, Jincheng,Yan, Hong,Zheng, Yang,Zhang, Guoqi
, p. 4697 - 4703 (2015/05/13)
A new approach to the selective synthesis of (E)-vinyl sulfones has been developed via a Fe/Cu co-catalyzed sulfonylation of arylpropiolic acid or phenylacetylene with sulfonyl hydrazides. A variety of vinyl sulfones have been obtained in moderate to good yields, comparable to the best results reported so far. The inexpensive Fe/Cu co-catalyzed method features a simple experimental procedure and good tolerance of substrate.
Iodine-mediated synthesis of (E)-vinyl sulfones from sodium sulfinates and cinnamic acids in aqueous medium
Gao, Jian,Lai, Junyi,Yuan, Gaoqing
, p. 66723 - 66726 (2015/08/24)
With water as the reaction medium, a green and efficient method has been developed for the synthesis of (E)-vinyl sulfones via I2-mediated decarboxylative cross-coupling reactions of sodium sulfinates with cinnamic acids. This synthetic route could effectively avoid the use of toxic organic solvents and transition metal catalysts, and the target products could be obtained with moderate to excellent yields under green and mild conditions.
