- 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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- PhB(OH)2-Promoted Electrochemical Sulfuration-Formyloxylation of Styrenes and Selectfluor-Mediated Oxidation-Olefination
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We report a PhB(OH)2-promoted electrochemical sulfuration-formyloxylation reaction of styrenes employing commercially available thiophenols/thiols as thiolating agents. Specifically, metal catalysts and external chemical oxidants are not needed in the reaction for the formation of β-formyloxy sulfides, and these sulfides can be further converted to (E)-vinyl sulfones via the Selectfluor-mediated oxidation-olefination. Notably, on the basis of this electrochemical oxidation strategy, β-hydroxy sulfide, β-formyloxy sulfoxide, β-formyloxy sulfone, and (E)-vinyl sulfoxide can also be easily prepared.
- Zhao, Yulei,Guo, Xuqiang,Li, Shuai,Fan, Yuhang,Sun, Xuejun,Tian, Laijin
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p. 9140 - 9145
(2021/11/30)
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- 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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- Photocatalyst-free visible light driven synthesis of (E)-vinyl sulfones from cinnamic acids and arylazo sulfones
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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
- Chawla, Ruchi,Jaiswal, Shefali,Dutta,Yadav, Lal Dhar S.
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supporting information
(2020/04/15)
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- Base-controlled divergent synthesis of vinyl sulfones from (benzylsulfonyl)benzenes and paraformaldehyde
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A tuneable metal-free protocol for the selective preparation of a-substituted vinyl sulfone and (E)-vinyl sulfone derivatives has been described. In this process, stable paraformaldehyde was used as the carbon source. The base played an important role in the selectivity control of transformations. More than 50 products were synthesized with excellent chemoselectivity and broad functional group tolerance.
- Xiao, Fuhong,Hu, Yangling,Huang, Huawen,Xu, Fen,Deng, Guo-Jun
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p. 3527 - 3535
(2020/05/25)
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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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- 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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p. 8791 - 8795
(2020/11/30)
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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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- 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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- Aerobic Copper-Catalyzed Synthesis of (E)-Vinyl Sulfones by Direct C-S Bond Oxidative Coupling
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Copper-catalyzed aerobic oxidative C-S bond coupling reaction between thiophenols and aryl-substituted alkenes for (E)-vinyl sulfones synthesis is reported here. With air utilized as a green oxidant, this transformation not only produces various vinyl sulfones in moderate to good yields but also possesses a simple and ecofriendly system. To clarify the mechanism, kinetic experiments has been investigated.
- Liang, Xiao,Xiong, Mingteng,Zhu, Heping,Shen, Kexin,Pan, Yuanjiang
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p. 11210 - 11218
(2019/09/12)
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- Metal-free synthesis of (E)-vinyl sulfones via denitrative coupling reactions of β-nitrostyrenes with sodium sulfinates
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A practical metal-free procedure for the synthesis of (E)-vinyl sulfones has been developed through the coupling of β-nitrostyrenes with sodium sulfinates under microwave irradiation. This methodology provides a convenient and efficient approach to various (E)-vinyl sulfones from readily available starting materials with excellent regioselectivity. The present oxidative reaction involves an efficient denitrative radical cross-coupling of β-nitrostyrenes with sodium sulfinates via using AcOH as an additive.
- Hong, Guang-Feng,Yuan, Jin-Wei,Dong, Zhen-Hua,Xiao, Yong-Mei,Mao, Pu,Qu, Ling-Bo
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p. 771 - 779
(2018/10/15)
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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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- 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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- Copper-Catalyzed Sulfonylation of Alkenes and Amines by Using Thiosulfonates as a Sulfonylating Agent
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Synthetically and pharmaceutically useful vinyl sulfones and sulfonamides are synthesized by the direct coupling of thiosulfonates with alkenes and amines, respectively. Copper catalysts help to generate the sulfonyl group from thiosulfonates and to form the C(sp2)–S/N–S bonds of the organosulfur compounds. This paper discusses the scope of these reactions of aromatic and aliphatic thiosulfonates with alkenes and amines.
- Shyam, Pranab K.,Son, Soobin,Jang, Hye-Young
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p. 5025 - 5031
(2017/09/22)
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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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- 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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supporting information
p. 1100 - 1103
(2017/03/15)
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- (E)-alkenyl sulfone compound and preparation method thereof
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The present invention relates to a (E)-alkenyl sulfone compound and a preparation method thereof. The preparation method comprises: dissolving a benzenesulfonyl hydrazide-based substrate and a phenylpropiolic acid substrate in an organic solvent, adding a
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Paragraph 0066-0068; 0078-0079
(2017/10/07)
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- Tetrabutylammonium Iodide Mediated Synthesis of β-Alkoxy Sulfides and Vinyl Sulfones by Using Benzenesulfonyl Chlorides as the Sulfur Sources under Acidic or Alkaline Conditions
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The tetrabutylammonium iodide (TBAI)-promoted generation of sulfur-containing compounds from benzenesulfonyl chlorides and alkenes is described. Under acidic condition, a wide range of β-alkoxy sulfides were obtained in good to excellent yields, whereas under alkaline conditions, various vinyl sulfones were produced in moderate to good yields. A novel preparation of (E)-β-iodovinyl sulfones was achieved through direct difunctionalization of alkynes with benzenesulfonyl chlorides and TBAI.
- Wang, Dingyi,Zhang, Rongxing,Lin, Sen,Yan, Zhaohua,Guo, Shengmei
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p. 2003 - 2008
(2016/08/09)
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- Visible-Light-Enabled Decarboxylative Sulfonylation of Cinnamic Acids with Sulfonylhydrazides under Transition-Metal-Free Conditions
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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.
- Cai, Shunyou,Xu, Yaohui,Chen, Danling,Li, Lihuang,Chen, Qifa,Huang, Mingqiang,Weng, Wen
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supporting information
p. 2990 - 2993
(2016/07/06)
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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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- Visible Light-Mediated Metal-Free Synthesis of Vinyl Sulfones from Aryl Sulfinates
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Visible light and eosin Y catalyze the synthesis of vinyl sulfones from aryl sulfinates and alkenes by a photoredox process. The reaction scope is broad in aryl sulfinates and alkenes and the general and simple procedure provides a metal-free alternative for the synthesis of synthetically valuable vinyl sulfones.
- Meyer, Andreas Uwe,J?ger, Stefanie,Prasad Hari, Durga,K?nig, Burkhard
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p. 2050 - 2054
(2015/06/23)
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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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- Phosphoric Acid-Mediated Synthesis of Vinyl Sulfones through Decarboxylative Coupling Reactions of Sodium Sulfinates with Phenylpropiolic Acids
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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.
- Rong, Guangwei,Mao, Jincheng,Yan, Hong,Zheng, Yang,Zhang, Guoqi
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p. 7652 - 7657
(2015/08/18)
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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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- Transition-metal-free synthesis of vinyl sulfones via tandem cross-decarboxylative/coupling reactions of sodium sulfinates and cinnamic acids
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A transition-metal-free synthesis of vinyl sulfones, utilizing sodium sulfinates and cinnamic acids through tandem cross-decarboxylative/coupling reactions, has been developed. This transformation is simple, efficient and environmentally benign, with a wide range of substrate scope and exceptional functional group tolerance. This journal is the Partner Organisations 2014.
- Xu, Yanli,Tang, Xiaodong,Hu, Weigao,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 3720 - 3723
(2014/08/05)
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- Chemoselective synthesis of unsymmetrical internal alkynes or vinyl sulfones via palladium-catalyzed cross-coupling reaction of sodium sulfinates with alkynes
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A highly efficient and mild palladium-catalyzed cross-coupling of sodium sulfinates and alkynes for the selective synthesis of unsymmetrical internal alkynes and vinyl sulfones has been developed. This methodology has advantages of easily accessible starting materials, functional group tolerance and a wide range of substrates, which provides rapid access to alkynes and vinyl sulfones.
- Xu, Yanli,Zhao, Jinwu,Tang, Xiaodong,Wu, Wanqing,Jiang, Huanfeng
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p. 2029 - 2039
(2014/07/07)
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- Aerobic copper-catalyzed synthesis of (E)-alkenyl sulfones and (E)-β-halo-alkenyl sulfones via addition of sodium sulfinates to alkynes
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Copper-catalyzed sulfonylation of alkynes using sodium sulfinates in air produced regio- and stereoselectively (E)-alkenyl sulfones. When a CuCl catalyst was employed, the hydrosulfonylation proceeded syn-selectively, and (E)-alkenyl sulfones were synthesized in excellent yields. In contrast, the reaction using CuI catalyst produced (E)-β-haloalkenyl sulfones anti-selectively in the presence of potassium halides. Furthermore, the (E)-β-bromoalkenyl sulfones are possible to convert into various alkenyl sulfones by Suzuki-Miyaura coupling.
- Taniguchi, Nobukazu
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supporting information
p. 1984 - 1990
(2014/03/21)
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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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- Metal-free, one-pot highly selective synthesis of (E)-vinyl sulfones and sulfoxides via addition-oxidation of thiols with alkynes
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We have developed a highly selective one-pot method for the synthesis of (E)-vinyl sulfones and sulfoxides from thiols with terminal alkynes. The sulfones and sulfoxides could be obtained with excellent selectivity in good isolated yields. It is simple, e
- Xue, Qicai,Mao, Zhijie,Shi, Yan,Mao, Haibin,Cheng, Yixiang,Zhu, Chengjian
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supporting information; experimental part
p. 1851 - 1854
(2012/04/23)
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- Copper-catalyzed oxidative hydrosulfonylation of alkynes using sodium sulfinates in air
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Copper-catalyzed hydrosulfonylations of alkynes can be carried out using sodium sulfinates in air. The procedure affords syn-selectively (E)-alkenyl sulfones in good yields. Then, both terminal and internal alkynes are available. Georg Thieme Verlag Stuttgart · New York.
- Taniguchi, Nobukazu
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supporting information; experimental part
p. 1245 - 1249
(2012/06/15)
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