69957-45-5Relevant articles and documents
A photocatalyst-free visible-light-mediated solvent-switchable route to stilbenes/vinyl sulfones from β-nitrostyrenes and arylazo sulfones
Chawla, Ruchi,Dutta, P. K.,Jaiswal, Shefali,Yadav, Lal Dhar S.
supporting information, p. 6487 - 6492 (2021/08/03)
Photocatalyst-free visible-light-mediated reactions, based on the presence of a visible-light-absorbing functional group in the starting material itself in order to exclude the often costly, hazardous, degradable and difficult to remove or recover photoredox catalysts, have been gaining momentum recently. We have employed this approach to develop a denitrative photocatalyst-free visible-light-mediated protocol for the arylation/sulfonylation of β-nitrostyrenes employing arylazo sulfones (bench-stable photolabile compounds) in a switchable solvent-controlled manner. Arylazo sulfones served as the aryl and sulfonyl radical precursors under blue LED irradiation for the synthesis oftrans-stilbenes and (E)-vinyl sulfones in CH3CN and dioxane/H2O 2?:?1, respectively. The absence of any metal, photocatalyst and additive; excellent selectivity (E-stereochemistry) and solvent-switchability; and the use of visible light and ambient temperature are the prime assets of the developed method. Moreover, we report the first photocatalyst-free visible light-driven route to synthesize stilbenes and vinyl sulfones from readily available β-nitrostyrenes.
Photocatalyst-free visible light driven synthesis of (E)-vinyl sulfones from cinnamic acids and arylazo sulfones
Chawla, Ruchi,Jaiswal, Shefali,Dutta,Yadav, Lal Dhar S.
supporting information, (2020/04/15)
A photocatalyst-free visible light mediated decarboxylative sulfono functionalization protocol has been explored for the synthesis of (E)-vinyl sulfones from cinnamic acids and bench-stable arylazo sulfones. The latter have been utilized as sulfonyl radic
Direct C-H Methylsulfonylation of Alkenes with the Insertion of Sulfur Dioxide
He, Fu-Sheng,Gong, Xinxing,Rojsitthisak, Pornchai,Wu, Jie
, p. 13159 - 13163 (2019/10/08)
The direct C-H methylsulfonylation of alkenes using inorganic sodium metabisulfite as the sulfur dioxide surrogate is described. This method provides convenient access to (E)-2-methyl styrenyl sulfones in good yields. In general, the in situ generated met
Stereoselective Synthesis of Alkenyl Silanes, Sulfones, Phosphine Oxides, and Nitroolefins by Radical C-S Bond Cleavage of Arylalkenyl Sulfides
Lin, Ya-mei,Lu, Guo-ping,Wang, Rong-kang,Yi, Wen-bin
, p. 1100 - 1103 (2017/03/15)
A radical-mediated approach has been introduced for the C-S bond activation of arylalkenyl sulfides. The protocol provides an efficient approach for the generation of various alkenes including alkenyl silanes, sulfones, phosphine oxides, and nitroolefins. In most cases, these radical substitutions are performed under metal-free conditions with stereospecificity.
Eosin Y (EY) Photoredox-Catalyzed Sulfonylation of Alkenes: Scope and Mechanism
Meyer, Andreas Uwe,Straková, Karolína,Slanina, Tomá?,K?nig, Burkhard
supporting information, p. 8694 - 8699 (2016/07/07)
Alkyl- and aryl vinyl sulfones were obtained by eosin Y (EY)-mediated visible-light photooxidation of sulfinate salts and the reaction of the resulting S-centered radicals with alkenes. Optimized reaction conditions, the sulfinate and alkene scope, and X-ray structural analyses of several reaction products are provided. A detailed spectroscopic study explains the reaction mechanism, which proceeds through the EY radical cation as key intermediate oxidizing the sulfinate salts.
CuSO4?·5H2O-H-phosphonate-catalyzed intermolecular C-S bond formation: Synthesis of (E)-vinyl alkylsulfones from alkynes and DMSO
Chen, Jian-Yu,Chen, Xiao-Lan,Li, Xu,Qu, Ling-Bo,Zhang, Qing,Duan, Li-Kun,Xia, Ying-Ya,Chen, Xin,Sun, Kai,Liu, Zhi-Dong,Zhao, Yu-Fen
supporting information, p. 314 - 319 (2015/02/02)
A CuSO4?·5H2O-H-phosphonate-catalyzed synthesis of (E)-vinyl alkylsulfones from alkynes and widely available DMSO was developed. The present protocol provides an alternative approach to various vinyl sulfones, with the advantages of cheap catalysts, readily available starting materials, operational simplicity and high stereo- and regioselectivity.
Ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones
Gao, Xiaofang,Pan, Xiaojun,Gao, Jian,Huang, Huawen,Yuan, Gaoqing,Li, Yingwei
supporting information, p. 210 - 212 (2015/01/09)
A novel ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones is described. The process proceeded smoothly under metal-free conditions with high stereoselectivity and good functional group toler
Catalytic and direct methyl sulfonylation of alkenes and alkynes using a methyl sulfonyl radical generated from a DMSO, dioxygen and copper system
Jiang, Yaojia,Loh, Teck-Peng
, p. 4939 - 4943 (2015/01/09)
This paper describes an efficient method to β-keto methyl sulfones and (E)-vinyl methyl sulfones using DMSO as the substrate. The methyl sulfonyl radical generated from DMSO in the presence of catalytic Cu(i) under O2 atmosphere is believed to be involved in this reaction. Isotopic labeling and 18O2 experiments were performed to investigate the reaction mechanism.
The first nucleophilic substitution reaction of organoindium reagents with sulfonyl chlorides: A facile method for preparation of vinyl sulfones
Deng, Guisheng,Zou, Jingyuan
experimental part, p. 186 - 194 (2010/08/19)
The first nucleophilic substitution reaction of organoindium with sulfonyl chlorides has been exploited. This reaction of vinylindium, derived from terminal alkynes via hydroindation, with sulfonyl chlorides in the presence of Ag 2O provides ac
Anion-functionalized ionic liquids enhance the cui-catalyzed cross-coupling reaction of sulfinic acid salts with aryl halides and vinyl bromides
Bian, Ming,Xu, Fada,Ma, Cheng
, p. 2951 - 2956 (2008/03/13)
An easily accessible, anion-functionalized ionic liquid, 1-ethyl-3-methylimidazolium (S)-2-amino-3-methylbutyric acid salt, [emim][Val], has been demonstrated to be an efficient additive for the CuI-catalyzed coupling reaction of sulfinic acid salts with aryl iodides, aryl bromides and vinyl bromides, leading to the formation of sulfones in good yields. Georg Thieme Verlag Stuttgart.
