- Controlled Synthesis of β-Keto Sulfones and Vinyl Sulfones under Electrochemical Oxidation
-
Selective sulfonylation and oxosulfonylation of alkenes with sulfinates have been developed via anodic oxidation in an undivided cell. The novel electrosynthetic method provided β-keto sulfones and vinyl sulfones with good to excellent yields in the absence of any transition metal catalyst and oxidants. Mechanism studies show that two different pathways involved in these two transformations.
- Fang, Yang,Xu, Dongping,Yu, Yingliang,Tang, Rumeng,Dai, Shuaishuai,Wang, Zhenghua,Zhang, Wu
-
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- Generation of potent Nrf2 activators via tuning the electrophilicity and steric hindrance of vinyl sulfones for neuroprotection
-
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
-
-
- Visible-Light-Induced Three-Component Intermolecular Trifluoromethyl-Alkenylation Reactions of Unactivated Alkenes
-
Herein, we describe a practical protocol for efficient, mild, visible-light-induced three-component intermolecular trifluoromethyl-alkenylation reactions of unactivated alkenes. The protocol has good functional group tolerance and a broad substrate scope. Using this protocol, we not only introduced a trifluoromethyl group into alkenes but also converted unactivated alkenes to styrene-based activated alkenes, in addition to accomplishing late-stage functionalization of pharmaceutical intermediates. (Figure presented.).
- Guo, Yuan-Qiang,Wang, Kaihua,Wang, Ruiguo,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
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supporting information
p. 1651 - 1655
(2021/02/12)
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- Vinyl sulfone synthesisviacopper-catalyzed three-component decarboxylative addition
-
The synthesis of vinyl sulfone derivativesviathe reaction of arylpropiolic acids, K2S2O5, and aryl boronic acids is reported. The CuBr2/1,10-phenanthroline catalytic system in the presence of acetic acid provide
- An, Seunghwan,Lee, Sunwoo,Song, Kwang Ho
-
supporting information
p. 7827 - 7831
(2021/09/28)
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- Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants
-
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).
- Jeremias, Noah,Mohr, Lisa-Marie,Bach, Thorsten
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supporting information
p. 5674 - 5678
(2021/08/03)
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- Photocatalyst-free visible light driven synthesis of (E)-vinyl sulfones from cinnamic acids and arylazo sulfones
-
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.
-
supporting information
(2020/04/15)
-
- Base-controlled divergent synthesis of vinyl sulfones from (benzylsulfonyl)benzenes and paraformaldehyde
-
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
-
supporting information
p. 3527 - 3535
(2020/05/25)
-
- Dual ligand-promoted palladium-catalyzed nondirected C-H alkenylation of aryl ethers
-
Direct C-H functionalization of aryl ethers remains challenging owing to their low reactivity and selectivity. Herein, a novel strategy for nondirected C-H alkenylation of aryl ethers promoted by a dual ligand catalyst was demonstrated. This catalytic system readily achieved the highly efficient alkenylation of alkyl aryl ethers (anisole, phenetole, n-propyl phenyl ether, n-butyl phenyl ether and benzyl phenyl ether), cyclic aryl ethers (1,4-benzodioxan, 2,3-dihydrobenzofuran, dibenzofuran), and diphenyl oxides. Moreover, the proposed methodology was successfully employed for the late-stage modification of complex drugs containing the aryl ether motif. Interestingly, the compounds developed herein displayed fluorescent properties, which would facilitate their biological applications.
- Fu, Manlin,Liu, Jiang,Wang, Lei,Yin, Biao,Zhu, Qing
-
supporting information
p. 3293 - 3296
(2020/04/02)
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- N,N′-Disulfonylhydrazines: New sulfonylating reagents for highly efficient synthesis of (E)-vinyl sulfones at room temperature
-
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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- Aerobic Copper-Catalyzed Synthesis of (E)-Vinyl Sulfones by Direct C-S Bond Oxidative Coupling
-
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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- (E)-(2-(phenylsulfonyl)vinyl)benzene and derivative thereof, and synthesis method of (E)-(2-(phenylsulfonyl)vinyl)benzene and derivative thereof
-
The invention relates to a technical scheme that under the joint action of alkaline and N,N-dimethyl formamide, (E)-(2-(phenylsulfonyl)vinyl)benzene and a derivative thereof are efficiently synthesized from multiple components of benzyl compounds and para
- -
-
Paragraph 0054; 0057; 0058; 0059-0065; 0068; 0069
(2019/06/13)
-
- A Study of Graphene-Based Copper Catalysts: Copper(I) Nanoplatelets for Batch and Continuous-Flow Applications
-
The use of graphene derivatives as supports improves the properties of heterogeneous catalysts, with graphene oxide (GO) being the most frequently employed. To explore greener possibilities as well as to get some insights into the role of the different gr
- De Angelis, Sonia,Franco, Mario,Triminì, Alessandra,González, Ana,Sainz, Raquel,Degennaro, Leonardo,Romanazzi, Giuseppe,Carlucci, Claudia,Petrelli, Valentina,de la Esperanza, Alejandro,Go?i, Asier,Ferritto, Rafael,Ace?a, José Luis,Luisi, Renzo,Cid, M. Belén
-
supporting information
p. 3011 - 3018
(2019/08/20)
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- Synthesis of Vinyl Sulfones via I2-mediated Alkene Sulfonylations with Thiosulfonates
-
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
-
supporting information
p. 535 - 539
(2018/03/13)
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- Method for synthesizing (E)-(2-(phenylsulfonyl)vinyl)benzene and derivative thereof
-
The invention provides a method for synthesizing (E)-(2-(phenylsulfonyl)vinyl)benzene and a derivative thereof. The method adopts styrene or a derivative of styrene as a reactant A and sodium benzenesulfinate or a derivative of sodium benzenesulfinate as
- -
-
Paragraph 0039-0040
(2018/07/30)
-
- E -Selective synthesis of vinyl sulfones via silver-catalyzed sulfonylation of styrenes
-
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
-
supporting information
p. 5748 - 5751
(2018/08/21)
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- Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts
-
A series of 1-alkenyl aryl sulfides was synthesized from thiiranes and diaryliodonium salts in tetrahydrofuran in the presence of potassium tert -butoxide. The proposed reaction mechanism involves generation of benzynes from the diaryliodonium salts in the presence of the base. Then, nucleophilic attack of the benzynes by thiiranes, followed by hydrogen abstraction and ring opening of the generated thiiranium intermediates, provides the sulfides. These sulfides were further oxidized with performic acid to the corresponding sulfones. The current method provides a metal-free and safe method for the preparation of 1-alkenyl aryl sulfides and their sulfones.
- Dong, Jun,Xu, Jiaxi
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p. 2407 - 2415
(2018/04/16)
-
- (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
- -
-
Paragraph 0033-0038
(2017/10/07)
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- Copper-Catalyzed Sulfonylation of Alkenes and Amines by Using Thiosulfonates as a Sulfonylating Agent
-
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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- Donor–Acceptor Complex Enables Alkoxyl Radical Generation for Metal-Free C(sp3)–C(sp3) Cleavage and Allylation/Alkenylation
-
The alkoxyl radical is an essential and prevalent reactive intermediate for chemical and biological studies. Here we report the first donor–acceptor complex-enabled alkoxyl radical generation under metal-free reaction conditions induced by visible light. Hantzsch ester forms the key donor–acceptor complex with N-alkoxyl derivatives, which is elucidated by a series of spectrometry and mechanistic experiments. Selective C(sp3)-C(sp3) bond cleavage and allylation/alkenylation is demonstrated for the first time using this photocatalyst-free approach with linear primary, secondary, and tertiary alkoxyl radicals.
- Zhang, Jing,Li, Yang,Xu, Ruoyu,Chen, Yiyun
-
supporting information
p. 12619 - 12623
(2017/09/11)
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- Decarboxylative sulfonylation of arylpropiolic acids with sulfinic acids: synthesis of (E)-vinyl sulfones
-
Decarboxylative sulfonylation of arylpropiolic acids has been achieved by simply employing Na2CO3as a promoter and arenesulfinic acids as sulfonylating reagents. This simple and environmentally benign transformation offers an alternative approach and allows for easy and rapid synthesis of E-Vinyl sulfones from arylpropiolic acids and arenesufinic acids.
- Meesin, Jatuporn,Katrun, Praewpan,Reutrakul, Vichai,Pohmakotr, Manat,Soorukram, Darunee,Kuhakarn, Chutima
-
supporting information
p. 1440 - 1446
(2017/02/15)
-
- Tetrabutylammonium Iodide Mediated Synthesis of β-Alkoxy Sulfides and Vinyl Sulfones by Using Benzenesulfonyl Chlorides as the Sulfur Sources under Acidic or Alkaline Conditions
-
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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- PhI(OAc)2-mediated decomposition of N-arylsulfonyl hydrazones: metal-free synthesis of (E)-vinyl sulfones
-
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
- Luo, Zaigang,Fang, Yuyu,Zhao, Yu,Xu, Xuemei,Feng, Chengtao,Li, Zhong,Zhang, Xiaomei,He, Jie
-
supporting information
p. 4105 - 4108
(2016/08/18)
-
- Visible-Light-Enabled Decarboxylative Sulfonylation of Cinnamic Acids with Sulfonylhydrazides under Transition-Metal-Free Conditions
-
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
-
supporting information
p. 2990 - 2993
(2016/07/06)
-
- Mn(III)-mediated regioselective synthesis of (: E)-vinyl sulfones from sodium sulfinates and nitro-olefins
-
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)
-
- Silver-Catalyzed Denitrative Sulfonylation of β-Nitrostyrenes: A Convenient Approach to (E)-Vinyl Sulfones
-
The first utilization of β-nitrostyrenes (readily available by the Henry reaction) for a highly stereoselective, convenient, and catalytic synthesis of (E)-vinyl sulfones at room temperature was investigated. The protocol involves efficient silver-catalyz
- Keshari, Twinkle,Kapoorr, Ritu,Yadav, Lal Dhar S.
-
supporting information
p. 2695 - 2699
(2016/06/08)
-
- Electrosynthesis of (E)-Vinyl Sulfones Directly from Cinnamic Acids and Sodium Sulfinates via Decarboxylative Sulfono Functionalization
-
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
- Qian, Peng,Bi, Meixiang,Su, Jihu,Zha, Zhenggen,Wang, Zhiyong
-
p. 4876 - 4882
(2016/07/06)
-
- Efficient Synthesis of Vinyl Sulfones by Manganese-Catalyzed Decarboxylative Coupling of Cinnamic Acids with Aromatic Sulfinic Acid Sodium Salts
-
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
-
supporting information
p. 2695 - 2698
(2016/11/25)
-
- Stereoselective Synthesis of Z-α,β-Unsaturated Sulfones Using Peterson Reagents
-
New Peterson reagents were prepared by introducing alkyloxy groups on the silicon atom in order to fix the conformation of the sulfone anion. The reagents 1d and 1e reacted with a variety of aldehydes after the treatment with Li-base to give Z-α,β-unsaturated sulfones with up to >99:1 selectivity in good to excellent yields. For the reaction with aliphatic aldehydes, CPME (cyclopentyl methyl ether) is the choice of solvent, while DME (1,2-dimethoxyethane) gave higher selectivity for the reaction with aromatic aldehydes.
- Ando, Kaori,Wada, Tomohiro,Okumura, Miho,Sumida, Hiroshi
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p. 6026 - 6029
(2016/01/09)
-
- An efficient one-pot, three-component synthesis of vinyl sulfones via iodide-catalyzed radical alkenylation
-
An efficient one-pot, three-component synthesis of vinyl sulfones via iodide-catalyzed radical alkenylation using aryl diazonium salts, terminal alkenes and DABSO is reported. This protocol offers good yields and tolerates a broad range of functional groups. Based on the extensive control experiments, we propose a plausible radical mechanism.
- Fan, Weizheng,Su, Jiapeng,Shi, Dongyang,Feng, Bainian
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p. 6740 - 6743
(2015/08/24)
-
- Synthesis of vinyl sulfoxides using sulfinyl chlorides and olefins
-
A general method for synthesis of vinyl sulfoxides, using sulfinyl chlorides and olefins as starting materials and DBU as an HCl scavenger, has been developed. Vinyl sulfoxides were obtained from the ZnCl2 catalysed addition of sulfinyl chlorides to olefins followed by the elimination with DBU. However, the direct reaction of sulfinyl chlorides with olefins in the presence of DBU, usually leads to generation of vinyl sulfones. The sulfonyl radicals generated from the DBU-mediated disproportionation of the sulfinyl radicals undergo addition-elimination reaction with olefins to give vinyl sulfones.
- Ding, Xiancai,Wen, Jianming,Wang, Jianqiang,Yu, Jun,Li, Jing-Hua
-
p. 282 - 285
(2015/06/02)
-
- Phosphoric Acid-Mediated Synthesis of Vinyl Sulfones through Decarboxylative Coupling Reactions of Sodium Sulfinates with Phenylpropiolic Acids
-
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)
-
- Regioselective, One-Pot, Three-Component Synthesis of 1,3,4- and 1,3,5-Triarylpyrazoles from 1- and 2-Aryl-1-alkenyl Sulfones
-
A one-pot, three-component coupling of aldehydes with hydrazines and 1-aryl-1-alkenyl sulfones or 2-aryl-1-alkenyl sulfones for the regioselective synthesis of 1,3,4- and 1,3,5-triarylpyrazoles was developed. In our developed procedure, 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) worked as an effective oxidant, and the addition of an strong acid was not necessary. We synthesized 1,3,4- and 1,3,5-triarylpyrazoles containing acid-labile functionalities in a one-pot reaction in good yields.
- Fuse, Shinichiro,Sugiyama, Hirotaka,Kobayashi, Daisuke,Iijima, Yusuke,Matsumura, Keisuke,Tanaka, Hiroshi,Takahashi, Takashi
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p. 4756 - 4764
(2015/08/03)
-
- Iodine-promoted decarboxylative C-S cross-coupling of cinnamic acids with sodium benzene sulfinates
-
We have developed a practical example of metal-free iodine-promoted decarboxyltive couplings between cinnamic acids and sodium benzene sulfinates, which represents an effective synthesis of vinyl sulfones via C-S bond formation reaction.
- Chen, Jie,Mao, Jincheng,Zheng, Yang,Liu, Defu,Rong, Guangwei,Yan, Hong,Zhang, Cheng,Shi, Daqing
-
p. 5059 - 5063
(2015/06/25)
-
- An efficient and facile synthesis of vinyl sulfones via microwave-assisted copper triflate catalyzed hydrosulfonylation of alkynes
-
An efficient method has been described for the synthesis of vinyl sulfones via hydrosulfonylation of alkynes using sodium arene sulfinates catalyzed by Cu(OTf)2 under microwave irradiation. A variety of vinyl sulfones was obtained in good to ex
- Shelke, Ganesh M.,Kameswara Rao,Pericherla, Kasiviswanadharaju,Kumar, Anil
-
p. 2345 - 2349
(2015/08/06)
-
- Synthesis of vinylsulfones via palladium-catalyzed decarboxylative coupling of cinnamic acids with aromatic sulfinic acid sodium salts
-
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
-
p. 1377 - 1383
(2014/08/18)
-
- Copper-catalyzed aerobic decarboxylative sulfonylation of cinnamic acids with sodium sulfinates: Stereospecific synthesis of (E)-alkenyl sulfones
-
A copper-catalyzed aerobic decarboxylative sulfonylation of alkenyl carboxylic acids with sodium sulfinates is developed. This study offers a new and expedient strategy for stereoselective synthesis of (E)-alkenyl sulfones that are widely present in biolo
- Jiang, Qing,Xu, Bin,Jia, Jing,Zhao, An,Zhao, Yu-Rou,Li, Ying-Ying,He, Na-Na,Guo, Can-Cheng
-
p. 7372 - 7379
(2014/09/16)
-
- Copper-catalyzed highly selective direct hydrosulfonylation of alkynes with arylsulfinic acids leading to vinyl sulfones
-
A novel Cu-catalyzed direct hydrosulfonylation of alkynes with arylsulfinic acids for the synthesis of (E)-vinyl sulfones has been realized under mild conditions with 100% atom efficiency. The present protocol provides an attractive approach to various vinyl sulfones in good to excellent yields, with the advantages of operation simplicity, atom economy, and high stereo- and regioselectivities.
- Wei, Wei,Li, Jinli,Yang, Daoshan,Wen, Jiangwei,Jiao, Yueting,You, Jinmao,Wang, Hua
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p. 1861 - 1864
(2014/03/21)
-
- Photoredox α-vinylation of α-amino acids and N -aryl amines
-
A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C-H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.
- Noble, Adam,MacMillan, David W. C.
-
supporting information
p. 11602 - 11605
(2014/11/08)
-
- Silver(I)-mediated reaction of trimethylsilylated arylacetylenes with sulfonyl chlorides: Unexpected formation of vinyl sulfones
-
A novel reaction of trimethylsilylated arylacetylenes with sulfonyl chlorides was performed in the presence of silver nitrate or triflate. Conjugated vinyl sulfones as dramatic products were obtained in moderate yields and with Z-selectivity. A free radical mechanism has been proposed to account for the formation of the products.
- Deng, Gui Sheng,Sun, Teng Fei
-
p. 1115 - 1118,4
(2020/08/20)
-
- An efficient synthesis of vinyl sulfones from alkenes and aryl sulfinates
-
Vinyl sulfones have been efficiently synthesized by treatment of alkenes with sodium arene sulfinates using potassium iodide and sodium periodate in the presence of a catalytic amount of acetic acid at room temperature. The products are formed in high yie
- Das, Biswanath,Lingaiah, Maram,Damodar, Kongara,Bhunia, Nisith
-
experimental part
p. 2941 - 2944
(2011/10/19)
-
- The first nucleophilic substitution reaction of organoindium reagents with sulfonyl chlorides: A facile method for preparation of vinyl sulfones
-
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
- Deng, Guisheng,Zou, Jingyuan
-
experimental part
p. 186 - 194
(2010/08/19)
-
- 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
-
supporting information; experimental part
p. 5633 - 5641
(2010/12/25)
-
- Radical-mediated thiodesulfonylation of the vinyl sulfones: access to (α-fluoro)vinyl sulfides
-
Radical-mediated thiodesulfonylation of the vinyl and (α-fluoro)vinyl sulfones, derived from aldehydes and ketones, with aryl thiols in organic or aqueous medium provided access to vinyl and (α-fluoro)vinyl sulfides. The vinyl sulfides were formed predominantly with E stereochemistry independent of the stereochemistry of the starting vinyl sulfones.
- Sacasa, Pablo R.,Zayas, Jessica,Wnuk, Stanislaw F.
-
scheme or table
p. 5424 - 5427
(2009/12/06)
-
- Efficient palladium(II) catalysis under air. Base-free oxidative heck reactions at room temperature or with microwave heating
-
(Figure Presented) Scope and limitations of the base-free oxidative Heck reaction with arylboronic acids have been explored. Under our conditions, the dmphen-palladium(II)-catalyzed arylation proceeded with air or p-benzoquinone as reoxidants of palladium(0). We found that ambient temperature and mild aerobic conditions allow for the use of substrates sensitive to palladium(II)-catalyzed oxidation. Oxidative Heck couplings, employing different arylboronic acids, were smoothly and regioselectively conducted with both electron-rich and electron-poor olefins, providing high yields even with disubstituted butyl methacrylate, sensitive acrolein, and a vinylboronate ester. Controlled microwave processing was used to reduce reaction times from hours to minutes both in small scale and in 50 mmol scale batch processes.
- Lindh, Jonas,Enquist, Per-Anders,Pilotti, Ake,Nilsson, Peter,Larhed, Mats
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p. 7957 - 7962
(2008/02/13)
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- Anion-functionalized ionic liquids enhance the cui-catalyzed cross-coupling reaction of sulfinic acid salts with aryl halides and vinyl bromides
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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.
- Bian, Ming,Xu, Fada,Ma, Cheng
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p. 2951 - 2956
(2008/03/13)
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- CuI/L-proline potassium salt catalysed synthesis of vinyl sulfones via coupling reaction of vinyl bromides with sulfinic acid salts in ionic liquid
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Catalysed by CuI/L-proline potassium salt, which serves as both base and ligand, the coupling reaction of vinyl bromides with sulfinic acid salts occurs at 110°C in ionic liquid to give the corresponding vinyl sulfones in good yields.
- Bao, Weiliang,Wang, Congna
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p. 396 - 397
(2007/10/03)
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- Heck vinylations using vinyl sulfide, vinyl sulfoxide, vinyl sulfone, or vinyl sulfonate derivatives and aryl bromides catalyzed by a palladium complex derived from a tetraphosphine
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The adverse impact of sulfur compounds on catalytic performance is well known. The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis[(diphenylphosphino) methyl]cyclopentane in combination with allylchloropalladium dimer affords an efficient catalyst for the Hec
- Battace, Ahmed,Zair, Touriya,Doucet, Henri,Santelli, Maurice
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p. 3495 - 3505
(2008/02/10)
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- Convenient synthesis of α,β-unsaturated sulfones via a Mizoroki-Heck reaction of arylboronic acids with phenyl vinyl sulfones
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Palladium acetate catalyzed Mizoroki-Heck reaction of arylboronic acids with phenyl vinyl sulfones afford α,β-unsaturated sulfones in good yields.
- Kabalka, George W.,Guchhait, Sankar K.
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p. 4021 - 4022
(2007/10/03)
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- Palladium-catalyzed cascade reaction of α,β-unsaturated sulfones with aryl iodides
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Unlike traditionally used acyclic 1,2-disubstituted alkenes, the reaction of α,β-unsaturated phenyl sulfones with aryl iodides under Heck reaction conditions (Pd(OAc)2 as catalyst, Ag2-CO3 as base in DMF at 120°C) takes place mainly by a cascade process, involving one unit of the alkene and three units of the aryl iodide, to afford a substituted 9-phenylsulfonyl-9,10-dihydrophenanthrene, The dominant formation of this 3:1 coupling product, instead of the Heck trisubstituted olefin, shows that aromatic C-H activation processes can compete with the usually fast syn β-hydrogen elimination step in the Heck arylation of an acyclic olefin. The structural scope of this palladium-catalyzed cascade arylation of α,β-unsaturated sulfones has proved to be wide with regard to substitution at the β-position (alkyl, aryl, or alkenyl substitution), substitution at the sulfone unit (alkyl or phenyl sulfones), and configuration at the C=C bond (trans or cis). Moreover, although less favored than in the case of the arylation of α,β-unsaturated sulfones, similarly substituted 9,10-dihydrophenanthrenes have also been obtained in the case of α,β-unsaturated phosphine oxides and α,β-unsaturated phosphonate esters. A Pd0-pdII-pdIV mechanistic pathway involving the successive formation of highly electrophilic σ-alkylpalladium intermediates and palladacycles is proposed for this multi-component arylation.
- Mauleon, Pablo,Nunez, Angel A.,Alonso, Ines,Carretero, Juan C.
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p. 1511 - 1520
(2007/10/03)
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- Studies on hydrozirconation of 1-alkynyl sulfoxides or sulfones and the application for the synthesis of stereodefined vinyl sulfoxides or sulfones
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The hydrozirconation reaction of 1-alkynyl sulfoxides or sulfones with CP2Zr(H)Cl in THF at room temperature predominantly gave Z-β-zirconated vinyl sulfoxides or sulfones with excellent regioselectivity. Compared with 1-alkynyl sulfoxides, the hydrozirconation reaction of 1-alkynyl sulfones exhibits great synthetic potential, leading to the efficient preparation of Z-β-halovinyl sulfones, Z-β-sulfonyl α,β-unsaturated ketones, and Z-β-alkynyl vinyl sulfones. Although the reaction mechanisms are still not clear, the neighboring group participation of the sulfinyl or sulfonyl group may be playing an important role in this unique hydrozirconation reaction.
- Huang, Xian,Duan, Dehui,Zheng, Weixin
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p. 1958 - 1963
(2007/10/03)
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