- Generation of potent Nrf2 activators via tuning the electrophilicity and steric hindrance of vinyl sulfones for neuroprotection
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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.
- Song, Zi-Long,Hou, Yanan,Bai, Feifei,Fang, Jianguo
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- Copper-Catalyzed Heck-Type Couplings of Sulfonyl Chlorides with Olefins: Efficient and Rapid Access to Vinyl Sulfones
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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.
- Chen, Qiulin,Liu, Lixia,Wang, Chengming,Xue, Pan
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supporting information
(2021/08/27)
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- Cu-catalyzed dehydrogenative olefinsulfonation of Alkyl arenes
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A copper-catalyzed reaction protocol for the dehydrogenation of ethylbenzenes into styrene derivatives has been developed. This reaction procedure proceeded well under mild reaction conditions, providing a practical and efficient strategy for the rapid assembly of biologically and pharmaceutically significant molecules, such as vinyl sulfone. Simple alkyl arenes were functionalized via consecutive β-elimination in the presence of N-sulfonylbenzo[d]imidazole with broad substrate scope and good functional group tolerance.
- Li, Fangfang,Zhang, Guang'an,Liu, Yingguo,Zhu, Bingke,Leng, Yuting,Wu, Junliang
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supporting information
p. 8791 - 8795
(2020/11/30)
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- N,N′-Disulfonylhydrazines: New sulfonylating reagents for highly efficient synthesis of (E)-vinyl sulfones at room temperature
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N,N′-Disulfonylhydrazines have been proven to be the most reactive precursors of sulfonyl radicals in all types of sulfonyl substituted hydrazines as early as a half century ago. But such function has not been applied in organic synthesis except the formation of disulfones by self-dimerization of sulfonyl radicals. In this article, they were introduced as new sulfonylating reagents and their combinations with NIS and Et3N were established as excellent iodosulfonylating reagents for alkenes. Finally, a highly efficient method for the synthesis of (E)-vinyl sulfones was developed by mixing an alkene, a N,N′-disulfonylhydrazine, NIS and Et3N in THF at room temperature for 5 min.
- Hu, Yuefei,Luo, Dongping,Min, Lin,Shan, Lidong,Wang, Xinyan,Zheng, Weiping
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- Electrochemical sulfonylation of alkenes with sulfonyl hydrazides: A metal- And oxidant-free protocol for the synthesis of (: E)-vinyl sulfones in water
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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
- Cai, Jianpeng,Guo, Huishi,Lai, Yin-Long,Liao, Jianhua,Luo, Jianmin,Mo, Yunyan,Yan, Shaoxi,Zhang, Shengling,Zhu, Lejie
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p. 33155 - 33160
(2020/10/05)
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- Electrochemical Synthesis of Vinyl Sulfones by Sulfonylation of Styrenes with a Catalytic Amount of Potassium Iodide
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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.
- Wang, Pei-Long,Gao, Hui,Jiang, Zhi-Sheng,Li, Chao,Tian, Zhi-Ao,Li, Pin-Hua
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supporting information
p. 1720 - 1724
(2020/09/21)
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- Electron Donor-Acceptor Complex Enabled Decarboxylative Sulfonylation of Cinnamic Acids under Visible-Light Irradiation
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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.
- Ge, Qian-Qian,Qian, Jia-Sheng,Xuan, Jun
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p. 8691 - 8701
(2019/08/30)
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- Radical Heck-type reaction of styrenes with sulfonyl hydrazides on water at room temperature
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Herein, metal-free radical Heck-type reaction of styrenes with sulfonyl hydrazides to synthesize vinyl sulfones is developed. The reaction is performed under economical TBAI/TBHP system on water in open air at room temperature, which proceeds through the
- Bao, Wen-Hui,Ying, Wei-Wei,Xu, Xu-Dong,Zhou, Guo-Dong,Meng, Xiao-Xiao,Wei, Wen-Ting,Liu, Yan-Yun,Li, Qiang
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supporting information
p. 55 - 58
(2018/11/30)
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- Copper(II) Acetate Mediated Synthesis of 3-Sulfonyl-2-aryl-2 H -chromenes
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This paper describes a concise, easy-operation, high-yielding method for the synthesis of 3-sulfonyl-2-aryl-2 H -chromenes by a one-pot, straightforward two-step synthetic route, which includes (i) Cu(OAc) 2 /PyBOP-mediated intermolecular [4+2] annulation of substituted salicylic acids with β-sulfonylstyrenes in the presence of DMAP in refluxing DMF, and (ii) sequential O -alkylation of the resulting sulfonylflavanones with n -butyl bromide. A plausible mechanism is proposed and discussed. This protocol provides a highly effective annulation via one carbon-oxygen (C-O) and one carbon-carbon (C-C) bond formations.
- Chang, Meng-Yang,Chen, Han-Yu,Chen, Yu-Hsin
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p. 3419 - 3430
(2019/09/07)
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- Synthetic method of (E)-alkenyl sulfone compounds
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The invention discloses a synthetic method of (E)-alkenyl sulfone compounds. The method comprises the following steps: beta-nitroolefin compounds shown as formula I in the description, sulfohydrazidecompounds shown as formula II in the description, an iodine-containing nonmetal catalyst and a peroxide oxidizing agent are mixed for a reaction, and a mixture obtained after the reaction is subjectedto postprocessing, and the (E)-alkenyl sulfone compounds shown as formula III in the description are obtained. Beta-nitroolefin compounds, the sulfohydrazide compounds, the iodine-containing nonmetalcatalyst and the peroxide oxidizing agent are taken as main raw materials, the corresponding (E)-alkenyl sulfone compounds are synthesized through free radical reaction, the iodine-containing nonmetal catalyst iodine or tetrabutylammonium iodide is used, the raw materials are simple, easily available, cheap, non-toxic and pollution-free to the environment, the dosage of the catalyst is small, thecatalyst has higher specificity for the reaction, synthetic reaction time can be shortened, the problem that the metal catalyst is difficult to separate in the prior art can be well solved, postprocessing difficulty is reduced, yield of the final product is increased, and purity of the final product is improved.
- -
-
Paragraph 0050-0051; 0053
(2019/01/14)
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- Metal-free catalyzed synthesis of the (E)-vinyl sulfones via aromatic olefins with arylsulfonyl hydrazides
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Synthesis of vinyl sulfones from aromatic olefins and arylsulfonyl hydrazides via I2-TBHP catalyzed system under the N2 atmosphere is described. Owing to no use of metal, only producing N2 and water as the byproducts and d
- Zhan, Zhenzhen,Ma, Haojie,Wei, Daidong,Pu, Jinghong,Zhang, Yixin,Huang, Guosheng
-
supporting information
p. 1446 - 1450
(2018/03/07)
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- Green preparation method for vinyl sulfone derivative in aqueous phase
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The invention relates to a green preparation method for a vinyl sulfone derivative in an aqueous phase. The method comprises the following steps: putting an olefin compound (1a), a sulfonyl hydrazidecompound of formula (2a) as shown in the specification, tetrabutylammonium iodide (TBAI), tert-butyl hydroperoxide (TBHP) and solvent water into a Schlenk reaction kettle, carrying out a stirring reaction on the reaction kettle at a certain temperature and an air atmosphere, monitoring the reaction process through TLC (Thin Layer Chromatography) or GC (Gas Chromatograph) till raw materials are completely reacted, and carrying out aftertreatment, thereby obtaining a target product, namely the vinyl sulfone derivative (I) as shown in the specification.
- -
-
Paragraph 0074-0076
(2018/11/22)
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- E -Selective synthesis of vinyl sulfones via silver-catalyzed sulfonylation of styrenes
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An efficient and highly E-selective protocol for the synthesis of vinyl sulfones is described. This simple protocol demonstrates the first synthesis of vinyl sulfones via a silver-catalyzed C-S bond coupling reaction. In addition, the success of the reaction was found to be critically dependent on the use of TEMPO as the additive.
- Gui, Qingwen,Han, Kang,Liu, Zhuoliang,Su, Zhaohong,He, Xiaoli,Jiang, Hongmei,Tian, Bufan,Li, Yangyan
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supporting information
p. 5748 - 5751
(2018/08/21)
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- Synthesis of Vinyl Sulfones via I2-mediated Alkene Sulfonylations with Thiosulfonates
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A simple sulfonylation strategy involving I2 and thiosulfonates, as sulfonyl-group precursors, is reported for the synthesis of vinyl sulfones. Sulfonyl radicals are presumed to be generated from thiosulfonates, which subsequently react with st
- Hwang, Sang Joon,Shyam, Pranab K.,Jang, Hye-Young
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supporting information
p. 535 - 539
(2018/03/13)
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- Stereoselective Synthesis of Alkenyl Silanes, Sulfones, Phosphine Oxides, and Nitroolefins by Radical C-S Bond Cleavage of Arylalkenyl Sulfides
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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.
- Lin, Ya-mei,Lu, Guo-ping,Wang, Rong-kang,Yi, Wen-bin
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p. 1100 - 1103
(2017/03/15)
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- Electrochemical Decarboxylative Sulfonylation of Cinnamic Acids with Aromatic Sulfonylhydrazides to Vinyl Sulfones
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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
- Zhao, Yu,Lai, Yin-Long,Du, Ke-Si,Lin, Dian-Zhao,Huang, Jing-Mei
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p. 9655 - 9661
(2017/09/23)
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- Copper(II)-Catalyzed Chemo- and Stereocontrolled Synthesis of (E)-Vinyl Sulfones and (Z)-β-Chlorovinyl Sulfones from Terminal Alkynes and Arylsulfonyl Hydrazides
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A facile copper(II)-catalyzed regio- and stereocontrolled synthesis of vinyl sulfones from terminal alkynes and arylsulfonyl hydrazides is described. Depending on the source of copper(II), two different kinds of vinyl sulfones, (E)-vinyl sulfones and (Z)-β-chlorovinyl sulfones were obtained and the addition of cyclohexanone played an important role in the reaction. These reactions display excellent chemoselectivity as well as stereoselectivity.
- Liu, Xiao-Tao,Ding, Zong-Cang,Ju, Lu-Chuan,Xu, Su-Xia,Zhan, Zhuang-Ping
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p. 1575 - 1582
(2017/03/21)
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- Electrosynthesis of vinyl sulfones from alkenes and sulfonyl hydrazides mediated by KI: Аn electrochemical mechanistic study
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A variety of vinyl sulfones were prepared from alkenes and sulfonyl hydrazides via electrochemical oxidative sulfonylation. The reaction proceeds in an experimentally convenient undivided electrochemical cell equipped with graphite and iron electrodes employing KI as a redox catalyst and a supporting electrolyte. Applying extremely high current density up to 270 mA/cm2 permits rapid synthesis in a compact reactor and with small surface area electrodes. A possible reaction mechanism was proposed with the use of cyclic voltammetry. It is the combination of anodic and cathodic processes in this reaction that makes it possible to obtain products under mild conditions with yields from moderate to high.
- Terent'ev, Alexander O.,Mulina, Olga M.,Pirgach, Dmitry A.,Ilovaisky, Alexey I.,Syroeshkin, Mikhail A.,Kapustina, Nadezhda I.,Nikishin, Gennady I.
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p. 6871 - 6879
(2017/11/06)
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- Metal-free Oxidative Coupling of Aromatic Alkenes with Thiols Leading to (E)-Vinyl Sulfones
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A facile I2O5-mediated direct oxidative coupling of aromatic alkenes with thiols toward vinyl sulfones has been developed under metal-free conditions. This methodology provides a convenient and efficient approach to various (E)-vinyl sulfones from readily available starting materials with excellent regioselectivity. The present oxidative coupling reaction, not only expands the scope of functionalization of alkenes with thiols, but also makes it a practical and powerful complement to traditional methods for the synthesis of (E)-vinyl sulfones.
- Wang, Leilei,Yue, Huilan,Yang, Daoshan,Cui, Huanhuan,Zhu, Minghui,Wang, Jinming,Wei, Wei,Wang, Hua
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p. 6857 - 6864
(2017/07/17)
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- Iodine-Catalyzed Facile Approach to Sulfones Employing TosMIC as a Sulfonylating Agent
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A novel iodine-catalyzed functionalization of a variety of olefins and alkynes and direct decarboxylative functionalization of cinnamic and propiolic acids with TosMIC to provide access to various vinyl, allyl, and β-iodo vinylsulfones is described. This simple, efficient, and environmentally benign approach employing inexpensive molecular iodine as a catalyst demonstrates a versatile protocol for the synthesis of highly valuable sulfones, rendering it attractive to both synthetic and medicinal chemistry.
- Kadari, Lingaswamy,Palakodety, Radha Krishna,Yallapragada, Lakshmi Prapurna
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supporting information
p. 2580 - 2583
(2017/05/24)
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- Mn(III)-mediated regioselective synthesis of (: E)-vinyl sulfones from sodium sulfinates and nitro-olefins
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An efficient Mn(iii)-mediated coupling reaction of sodium sulfinates with nitro-olefins has been developed, this reaction proceeds in mild and open-flask conditions to afford (E)-vinyl sulfones with high regioselectivities and in good to excellent yields. The control experiments revealed that this transformation could involve a radical process.
- Nie, Gang,Deng, Xiaocong,Lei, Xue,Hu, Qinquan,Chen, Yunfeng
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p. 75277 - 75281
(2016/08/24)
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- Efficient Synthesis of Vinyl Sulfones by Manganese-Catalyzed Decarboxylative Coupling of Cinnamic Acids with Aromatic Sulfinic Acid Sodium Salts
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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.
- Xue, Na,Guo, Ruqing,Tu, Xinman,Luo, Weiping,Deng, Wei,Xiang, Jiannan
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supporting information
p. 2695 - 2698
(2016/11/25)
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- A direct metal-free decarboxylative sulfono functionalization (DSF) of cinnamic acids to α,β-unsaturated phenyl sulfones
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A metal-free room temperature decarboxylative cross-coupling between cinnamic acids and arylsulfonyl hydrazides has been realized for the first time for the synthesis of (E)-vinyl sulfones. The scope and versatility of the reaction has been demonstrated by the regio- and stereoselective synthesis of 22 derivatives with diverse structural features.
- Singh, Rahul,Allam, Bharat Kumar,Singh, Neetu,Kumari, Kumkum,Singh, Satish Kumar,Singh, Krishna Nand
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supporting information
p. 2656 - 2659
(2015/06/16)
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- Iron/copper Co-catalyzed synthesis of vinyl sulfones from sulfonyl hydrazides and alkyne derivatives
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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.
- Rong, Guangwei,Mao, Jincheng,Yan, Hong,Zheng, Yang,Zhang, Guoqi
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p. 4697 - 4703
(2015/05/13)
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- Copper-catalyzed radical reaction of N -tosylhydrazones: Stereoselective synthesis of (E)-vinyl sulfones
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A new chemistry of hydrazines that is a copper-catalyzed radical reaction to synthesize vinyl sulfones from readily available N-tosylhydrazones has been described. The protocol provides a novel strategy for the synthesis of various vinyl sulfones including α, β-disubstituted ones and terminal ones. The advantages of the transformation include excellent E stereoselectivity, broad substrate scope, low cost of reagents, and convenient operation. A novel and efficient one-pot synthesis of alkynes from N-tosylhydrazones has been achieved. The studies provide important complementary approaches for the syntheses of vinyl sulfones and alkynes.
- Mao, Shuai,Gao, Ya-Ru,Zhu, Xue-Qing,Guo, Dong-Dong,Wang, Yong-Qiang
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p. 1692 - 1695
(2015/04/14)
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- Iodine-mediated synthesis of (E)-vinyl sulfones from sodium sulfinates and cinnamic acids in aqueous medium
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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.
- Gao, Jian,Lai, Junyi,Yuan, Gaoqing
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p. 66723 - 66726
(2015/08/24)
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- Metal-free iodine-mediated synthesis of vinyl sulfones at room temperature using water as solvent
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Metal-free efficient iodine-mediated synthesis of vinyl sulfones utilizing aryl sulfinates and alkenes has been realized under mild conditions in water. Notably, sodium methanesulfinate was used in this transformation, affording the β-iodo sulfones in goo
- Zhang, Ning,Yang, Daoshan,Wei, Wei,Yuan, Li,Cao, Youjuan,Wang, Hua
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p. 37013 - 37017
(2015/05/05)
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- FLUOROMETHYL-SUBSTITUTED PYRROLE CARBOXAMIDES III
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The invention relates to pyrrole carboxamides bearing a fluoromethyl- moiety as voltage gated calcium channel blockers, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pa
- -
-
Page/Page column 57
(2015/07/07)
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- FLUOROMETHYL-SUBSTITUTED PYRROLE CARBOXAMIDES IV
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The invention relates to pyrrole carboxamides bearing a fluoromethyl- moiety as voltage gated calcium channel blockers, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
- -
-
Page/Page column 50
(2015/07/07)
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- FLUOROMETHYL-SUBSTITUTED PYRROLE CARBOXAMIDES
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The invention relates to pyrrole carboxamides bearing a fluoromethyl-moiety as voltage gated calcium channel blockers, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
- -
-
-
- FLUOROMETHYL-SUBSTITUTED PYRROLE CARBOXAMIDES
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The invention relates to pyrrole carboxamides bearing a fluoromethyl- moiety as voltage gated calcium channel blockers, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
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- Synthesis of vinylsulfones via palladium-catalyzed decarboxylative coupling of cinnamic acids with aromatic sulfinic acid sodium salts
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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.]
- Guo, Ruqing,Gui, Qingwen,Wang, Dadian,Tan, Ze
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p. 1377 - 1383
(2014/08/18)
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- Revealing the metal-like behavior of iodine: An iodide-catalysed radical oxidative alkenylation
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In this work, we have described an alternative alkenylation approach to illustrate the metal-like behaviour of iodine in cross-coupling reactions. Alkenylation could proceed through iodide catalysed radical initiation, radical addition and iodine promoted
- Tang, Shan,Wu, Yong,Liao, Wenqing,Bai, Ruopeng,Liu, Chao,Lei, Aiwen
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supporting information
p. 4496 - 4499
(2014/04/17)
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- Copper-catalyzed aerobic oxidative N-S bond functionalization for C-S bond formation: Regio- and stereoselective synthesis of sulfones and thioethers
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A regio- and stereoselective synthesis of sulfones and thioethers by means of CuI-catalyzed aerobic oxidative N-S bond cleavage of sulfonyl hydrazides, followed by cross-coupling reactions with alkenes and aromatic compounds to form the C-sp-2-S bond, is described herein. N2 and H2O are the byproducts of this transformation, thus offering an environmentally benign process with a wide range of potential applications in organic synthesis and medicinal chemistry. First cleave, then cross-couple: A direct Cu-catalyzed aerobic oxidative C-sp-2-H functionalization and C-S bond coupling reaction has been developed (see scheme). By slight modification of the additive, sulfonyl hydrazides could serve as sulfonation, sulfenation, or arylation reagents to undergo cross-coupling reactions with alkenes and (hetero)aromatic cycles, affording sulfones, thioethers, and biaryl compounds with high regio- and stereoselectivities (see scheme).
- Li, Xianwei,Xu, Yanli,Wu, Wanqing,Jiang, Chang,Qi, Chaorong,Jiang, Huanfeng
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supporting information
p. 7911 - 7915
(2014/07/07)
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- Transition-metal-free synthesis of (E)-vinyl sulfones from vinyl halides in water
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A practical transition-metal-free procedure for the synthesis of (E)-vinyl sulfones through the coupling of vinyl halides with sodium sulfinates in water is reported. The reaction is strongly influenced by the presence of acids, and the use of nBu4NBr promotes its efficiency. A metal-free procedure for the synthesis of vinyl sulfones through the coupling of vinyl halides with sodium sulfinates in water is presented. The reaction is strongly influenced by the presence of acids, and the use of nBu4NBr promotes its efficiency. Copyright
- Liang, Shuai,Zhang, Ruo-Yi,Wang, Gao,Chen, Shan-Yong,Yu, Xiao-Qi
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supporting information
p. 7050 - 7053
(2013/11/06)
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- An improved synthesis of vinyl- and β-iodovinyl sulfones by a molecular iodine-mediated one-pot iodosulfonationdehydroiodination reaction
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An improved one-pot method to synthesize vinyl sulfones from unsaturated systems by using molecular iodine/sodium arenesulfinate/sodium acetate as reagents was described. Vinyl sulfones derived from styrene derivatives were generally obtained in good to excellent yields except for those bearing strong electron releasing substituent. Aliphatic alkenes and activated alkenes gave the corresponding vinyl sulfone products in moderate to good yields. Arylacetylenes yielded the respective β-iodovinyl sulfones in good yields while low yield was observed with aliphatic terminal alkyne. The potentials of the method entail simplicity, short reaction time, non-anhydrous reaction conditions, employing inexpensive, non-metallic reagent and integrating two reactions that are commonly accomplished separately into a single operation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Sawangphon, Tassaporn,Katrun, Praewpan,Chaisiwamongkhol, Korbua,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Soorukram, Darunee,Kuhakarn, Chutima
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supporting information
p. 1692 - 1707
(2013/05/22)
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- A one-pot regioselective synthetic route to vinyl sulfones from terminal epoxides in aqueous media
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A highly efficient LiBr catalysed regioselective synthesis of vinyl sulfones from readily available terminal epoxides and sodium sulfinates in a one-pot procedure using water as a reaction medium is reported. The protocol is adorned with several attributes of green chemistry like recycling of the catalyst, atom-economy and an aqueous medium.
- Chawla, Ruchi,Kapoor, Ritu,Singh, Atul K.,Yadav, Lal Dhar S.
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experimental part
p. 1308 - 1313
(2012/06/01)
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- Stereoselective synthesis of (E)-alkenyl sulfones from alkenes or alkynes via copper-catalyzed oxidation of sodium sulfinates
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Alkenyl sulfones can be stereoselectively synthesized from alkenes or alkynes using sodium sulfinates. The reaction can be performed by a copper-catalyzed oxidation of sodium sulfinates in air. The reaction of alkenes gives (E)-alkenyl sulfones via anti addition of sulfonyl cation and elimination process. Furthermore, the employment of alkynes produces (E) β- haloalkenyl sulfones in the presence of potassium halides. Georg Thieme Verlag Stuttgart · New York.
- Taniguchi, Nobukazu
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supporting information; experimental part
p. 1308 - 1312
(2011/07/07)
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- PhI(OAc)2/KI-mediated reaction of aryl sulfinates with alkenes, alkynes, and α,β-unsaturated carbonyl compounds: Synthesis of vinyl sulfones and β-iodovinyl sulfones
-
(Diacetoxyiodo)benzene [PhI(OAc)2, DIB] was able to promote the reaction of sodium aryl sulfinate and potassiumiodide (KI) with alkenes and alkynes to afford the corresponding vinyl sulfones and β-iodovinyl sulfones, respectively, in good yield
- Katrun, Praewpan,Chiampanichayakul, Supanimit,Korworapan, Kanokwan,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Kuhakarn, Chutima
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supporting information; experimental part
p. 5633 - 5641
(2010/12/25)
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- CAN mediated reaction of aryl sulfinates with alkenes and alkynes: Synthesis of vinyl sulfones, β-iodovinyl sulfones and acetylenic sulfones
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Cerium(IV) ammonium nitrate (CAN) mediated reaction of aryl sulfinates and sodium iodide with alkenes afforded vinyl sulfones in very good yields. Alkynes underwent similar reaction to give β-iodovinyl sulfones, which on treatment with potassium carbonate
- Nair, Vijay,Augustine, Anu,Suja
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p. 2259 - 2265
(2007/10/03)
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- An efficient one-pot synthesis of vinyl sulphones via CAN mediated reaction of aryl sulphinates and alkenes
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Cerium(IV) ammonium nitrate mediated reaction of sodium arene sulphinate and sodium iodide with alkenes afforded vinyl sulphones in very good yields.
- Nair, Vijay,Augustine, Anu,George, Tesmol G,Nair, Latha G
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p. 6763 - 6765
(2007/10/03)
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- Addition of Arenesulphonyl Iodides to Substituted Phenylacetylenes
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The products of the addition of toluene-p-sulphonyl iodide to substituted phenylacetylenes (and styrenes) are studied.The regiospecificity and stereoselectivity of trans addition to acetylenes is inferred from (1)H n.m.r. spectroscopy.The effect of substituents on the reactivity of substituted phenylacetylenes towards substituted beenzenesulphonyl radicals generated by photolysis of sulphonyl iodides is studied.Phenylacetylenes with electron-donating substituents react faster.Relative reactivities yield good Hammet-Brown correlations showing the electrophilic character of sulphonyl radicals towards phenylacetylenes.The selectivity of the addition (measured by ρ) of different sulphonyl radicals towards the same set of acetylenes ranges from -0.53 to -0.93 and shows a tendency to be smaller for benzenesulphonyl iodides carrying electron donating substituents.Results are discussed in terms of polar effects on the transition state and frontier molecular orbital theory.
- Silva Correa, Carlos M. M. da,Fleming, Maria Daniela C. M.
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p. 103 - 108
(2007/10/02)
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- Reactions of Arenesulfonyl Chlorides with Olefins Catalyzed by a Ruthenium(II) Complex
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Arenesulfonyl chlorides react with vinylarenes in the presence of dichlorotris(triphenylphosphine)ruthenium(II) catalyst and 1 molar equiv of a tertiary amine to form α,β-unsaturated sulfones 2.Only the E isomers of the sulfones are formed.In reactions of arenesulfonyl chlorides containing an electron-withdrawing Cl or NO2 substituent with α-methylstyrenes, 2-aryl-3-(arylsulfonyl)propenes (5) are also formed.Mechanisms for these reactions are proposed.
- Kamigata, Nobumasa,Sawada, Hideo,Kobayashi, Michio
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p. 3793 - 3796
(2007/10/02)
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