- Vinyl sulfone synthesisviacopper-catalyzed three-component decarboxylative addition
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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
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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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- 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
-
supporting information
p. 8791 - 8795
(2020/11/30)
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- 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
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p. 3527 - 3535
(2020/05/25)
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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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- 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
-
-
- Electrochemical sulfonylation of alkenes with sulfonyl hydrazides: A metal- And oxidant-free protocol for the synthesis of (: E)-vinyl sulfones in water
-
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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- (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; 0071
(2019/06/13)
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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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- Visible-light-induced decarboxylative sulfonylation of cinnamic acids with sodium sulfinates by using Merrifield resin supported Rose Bengal as a catalyst
-
A visible-light-induced decarboxylative sulfonylation of cinnamic acids with sodium sulfinates for the synthesis of vinyl sulfones was developed. The reaction proceeded smoothly in the presence of Merrifield resin supported Rose Bengal ammonium salt as a
- Li, Pinhua,Wang, Guan-Wu
-
supporting information
p. 5578 - 5585
(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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- Metal-free synthesis of (E)-vinyl sulfones via denitrative coupling reactions of β-nitrostyrenes with sodium sulfinates
-
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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- Preparation method of (E)-alkenyl sulfone compounds
-
The invention discloses a preparation method of (E)-alkenyl sulfone compounds. The method comprises the following steps: MeCN-H2O (3:1) is taken as a solvent, I2 and 30% H2O2 oxidize ketone or aldehyde (IV) in presence of p-TsOH, geminal diol peroxide compounds shown in formula (V) are generated in situ, the compounds in formula (V) taken as a peroxidation reagent and I2 are subjected to concertedcatalysis of a reaction between aryl ene compounds (II) and sulfohydrazide compounds (III), and the (E)-alkenyl sulfone compounds (I) are prepared. The method has the beneficial effects that the peroxidation reagent geminal diol peroxide compounds (V) are generated in situ, and operation is safe; iodide ions generated after I2 reaction are reoxidized by H2O2 in the presence of p-TsOH, and I2 is generated in situ and is involved in the reaction cyclically.
- -
-
Paragraph 0012
(2019/01/14)
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- 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
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supporting information
p. 5748 - 5751
(2018/08/21)
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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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- 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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- Electrochemical Decarboxylative Sulfonylation of Cinnamic Acids with Aromatic Sulfonylhydrazides to Vinyl Sulfones
-
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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- 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)
-
- Method for selectively synthesizing (E)-vinyl sulphone compound by using manganese salts
-
The invention relates to a method for selectively synthesizing a (E)-vinyl sulphone compound by using manganese salts, and belongs to the technical field of organic and medicine synthesis. The method comprises the following steps: adding nitroolefin and s
- -
-
Paragraph 0023; 0024
(2017/08/27)
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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)
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- 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
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supporting information
p. 2990 - 2993
(2016/07/06)
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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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- Silver-Catalyzed Denitrative Sulfonylation of β-Nitrostyrenes: A Convenient Approach to (E)-Vinyl Sulfones
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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)
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- Electrosynthesis of (E)-Vinyl Sulfones Directly from Cinnamic Acids and Sodium Sulfinates via Decarboxylative Sulfono Functionalization
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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
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p. 4876 - 4882
(2016/07/06)
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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
-
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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- Metal-free iodine-mediated synthesis of vinyl sulfones at room temperature using water as solvent
-
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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- 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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- 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
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p. 5059 - 5063
(2015/06/25)
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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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- PhI(OAc)2 mediated decarboxylative sulfonylation of β-aryl-α,β-unsaturated carboxylic acids: A synthesis of (E)-vinyl sulfones
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A highly efficient metal-free decarboxylative sulfonylation protocol for the preparation of (E)-vinyl sulfones from of β-aryl-α,β-unsaturated carboxylic acids using sodium sulfinates and (diacetoxyiodo)benzene (PhI(OAc)2) was developed. This strategy offers a simple and expedient synthesis of (E)-vinyl sulfones bearing a wide variety of functional groups. A radical-based pathway has been proposed for this decarboxylative sulfonylation reaction.
- Katrun, Praewpan,Hlekhlai, Sornsiri,Meesin, Jatuporn,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Soorukram, Darunee,Kuhakarn, Chutima
-
supporting information
p. 4785 - 4794
(2015/04/27)
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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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- Copper-catalyzed aerobic decarboxylative sulfonylation of cinnamic acids with sodium sulfinates: Stereospecific synthesis of (E)-alkenyl sulfones
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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
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p. 7372 - 7379
(2014/09/16)
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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
-
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
-
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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- 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)
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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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- 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
-
supporting information; experimental part
p. 1245 - 1249
(2012/06/15)
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- Stereoselective synthesis of (E)-alkenyl sulfones from alkenes or alkynes via copper-catalyzed oxidation of sodium sulfinates
-
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
-
supporting information; experimental part
p. 1308 - 1312
(2011/07/07)
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- Palladium-catalyzed desulfitative mizoroki-heck couplings of sulfonyl chlorides with mono-and disubstituted olefins: Rhodium-catalyzed desulfitative heck-type reactions under phosphine- And base-free conditions
-
New conditions have been found for the desulfitative Mizoroki-Heck arylation and trifluoromethylation of mono- and disubustituted olefins with arenesulfonyl and trifluoro-methanesulfonyl chlorides. Thus (E)-1,2- disubstituted alkenes with high ster-eoselectivity and 1,1,2-disubstituted alkenes with 12:1 to 21:1 E/Z steroselectivity can be obtained. Herrmann's palladacycle at 0.1 mol% is sufficient to catalyze these reactions, for which electron-rich or electron-poor sulfonyl chlorides and alkenes are suitable. If phosphine- and base-free conditions are required. 1 mol% [RriCl(C 2,H4)2] catalyzes the desulfitative cross-cou pling reactions. Contrary to results reported for [RuCl2(PPh 3)2]-catalyzed coupling reactions with sulfonyl chlorides, the palladium and rhodium desulfitative Mizoroki-Heck coupling reactions are not inhibited by radical scavenging agents. Possible sulfones arising from the sulfonylation of alkenes at 60°C are not desulfitated at higher temperatures in the presence of the Pd or Rh catalysts.
- Dubbaka, Srinivas Reddy,Vogel, Pierre
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p. 2633 - 2641
(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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- The synthesis of ethenyl bifunctional reagents containing a sulfone moiety and zirconium by the abnormal addition of Cp2Zr(H)Cl to internal acetylenic sulfones
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Ethenyl bifunctional reagents containing a sulfone moiety and zirconium are prepared by the abnormal addition of Cp2Zr(H)Cl to internal acetylenic sulfones.
- Huang, Xian,Duan, De-Hui
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p. 1741 - 1742
(2007/10/03)
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- Palladium-Catalyzed Cross-Coupling of Organostannanes with Sulfonyl Chlorides: A Simple Synthesis of Sulfones
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The palladium-catalyzed cross-coupling reaction between aryl- and alkylsulfonyl chlorides and substituted vinyl- and allylstannanes proceeds smoothly to provide good yields of sulfones and tolerates a wide variety of functionalities.
- Labadie, Sharada S.
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p. 2496 - 2498
(2007/10/02)
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- Conjugate Addition Reactions of α,β-Unsaturated Ketones with Higher Order, Mixed Organocuprate Reagents, R2Cu(CN)Li2
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Conjugate reactions of mixed cuprates R2Cu(CN)Li2 with α,β-unsaturated ketones are reported.These reagents, in most cases, react extremely rapidly affording the corresponding alkylated ketones in high yields.Attempts at trapping the intermediate enolates appeared to be successful using MeI as electrophile; however, the method is not general and was, therefore, not pursued.The effects of solvent and ligand composition on R2Cu(CN)Li2 as well as on the more highly mixed species RTRRCu(CN)Li2 have been examined.The selectivity of ligand transfer in these latter,second generation organocuprates is also discussed.
- Lipshutz, Bruce H.,Wilhelm, Robert S.,Kozlowski, Joseph A.
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p. 3938 - 3942
(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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