41173-24-4Relevant academic research and scientific papers
Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants
Jeremias, Noah,Mohr, Lisa-Marie,Bach, Thorsten
supporting information, p. 5674 - 5678 (2021/08/03)
2-Aryl-1-sulfonyl-substituted cyclobutanes were prepared in an intermolecular [2 + 2] photocycloaddition from various α,β-unsaturated sulfones and olefins upon irradiation at λ = 300 nm (26 examples, 60-99% yield). Lewis acids catalyzed the [2 + 2] photocycloaddition of 2-benzimidazolyl styryl sulfones. At short wavelengths, the latter substrates underwent C-S bond cleavage but AlBr3 (5 mol %) allowed for an intermolecular reaction with 2,3-dimethyl-2-butene at longer wavelengths. A chiral-at-metal Lewis acid (2 mol %) facilitated an enantioselective reaction (up to 77% ee).
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.
Visible-light-induced decarboxylative sulfonylation of cinnamic acids with sodium sulfinates by using Merrifield resin supported Rose Bengal as a catalyst
Li, Pinhua,Wang, Guan-Wu
supporting information, p. 5578 - 5585 (2019/06/13)
A visible-light-induced decarboxylative sulfonylation of cinnamic acids with sodium sulfinates for the synthesis of vinyl sulfones was developed. The reaction proceeded smoothly in the presence of Merrifield resin supported Rose Bengal ammonium salt as a
A mild light-induced cleavage of the S-O bond of aryl sulfonate esters enables efficient sulfonylation of vinylarenes
Ratushnyy, Maxim,Kamenova, Monika,Gevorgyan, Vladimir
, p. 7193 - 7197 (2018/10/02)
A new mode of S-O bond activation has been discovered, which constitutes novel reactivity of easily available and bench-stable arylsulfonate phenol esters. This protocol enables access to putative sulfonyl radical intermediates, which enable straightforward access to valuable vinyl sulfones.
Electrosynthesis of (E)-Vinyl Sulfones Directly from Cinnamic Acids and Sodium Sulfinates via Decarboxylative Sulfono Functionalization
Qian, Peng,Bi, Meixiang,Su, Jihu,Zha, Zhenggen,Wang, Zhiyong
, p. 4876 - 4882 (2016/07/06)
A variety of (E)-vinyl sulfones were constructed directly from cinnamic acids and sodium sulfinates with high regioselectivity at room temperature by virtue of an electrocatalytic oxidation. A radical intermediate was detected, and the corresponding mecha
Efficient Synthesis of Vinyl Sulfones by Manganese-Catalyzed Decarboxylative Coupling of Cinnamic Acids with Aromatic Sulfinic Acid Sodium Salts
Xue, Na,Guo, Ruqing,Tu, Xinman,Luo, Weiping,Deng, Wei,Xiang, Jiannan
supporting information, p. 2695 - 2698 (2016/11/25)
An efficient synthesis of vinyl sulfones is described. Reactions of cinnamic acids with aromatic sulfinic acid sodium salts in the presence of a catalytic amount of manganese(II) acetate tetrahydrate (5 mol%) in dimethyl sulfoxide (DMSO) afforded the desired vinyl sulfones in good to excellent yields. Notably, the reaction does not need any base or iodide as additive. The use of DMSO as the solvent and running the reaction under air are critical in achieving good yields.
Visible-Light-Enabled Decarboxylative Sulfonylation of Cinnamic Acids with Sulfonylhydrazides under Transition-Metal-Free Conditions
Cai, Shunyou,Xu, Yaohui,Chen, Danling,Li, Lihuang,Chen, Qifa,Huang, Mingqiang,Weng, Wen
supporting information, p. 2990 - 2993 (2016/07/06)
Decarboxylative cross-coupling reactions of cinnamic acids with sulfonylhydrazides were explored using oxygen as the sole terminal oxidant, realizing a conceptually novel technology for vinyl sulfone synthesis under the synergistic interactions of visible light irradiation, organic dye-type photocatalyst eosin Y, KI, and Cs2CO3 at room temperature.
Phosphoric Acid-Mediated Synthesis of Vinyl Sulfones through Decarboxylative Coupling Reactions of Sodium Sulfinates with Phenylpropiolic Acids
Rong, Guangwei,Mao, Jincheng,Yan, Hong,Zheng, Yang,Zhang, Guoqi
, p. 7652 - 7657 (2015/08/18)
A novel phosphoric acid -mediated synthesis of vinyl sulfones through decarboxylative coupling reactions of sodium sulfinates with phenylpropiolic acids is described. This transformation is efficient and environmentally friendly.
Synthesis of vinylsulfones via palladium-catalyzed decarboxylative coupling of cinnamic acids with aromatic sulfinic acid sodium salts
Guo, Ruqing,Gui, Qingwen,Wang, Dadian,Tan, Ze
, p. 1377 - 1383 (2014/08/18)
A highly efficient synthesis of vinylsulfones was achieved via decarboxylative cross-coupling reaction of cinnamic acids with aromatic sulfinic acid sodium salts catalyzed by Pd(OAc)2 and dppb in the presence of Ag2CO3. The reaction was found to furnish various vinylsulfones in good yields instead of the expected desulfitative product stilbenes. Mechanistic investigation also suggested that the decarboxylation is likely to take place after the transmetallation step. Graphical Abstract: [Figure not available: see fulltext.]
