- PHOTODECOMPOSITION OF SELENOSULFONATES AND THEIR FACILE PHOTOADDITION TO ALKENES1
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Phenyl areneselenosulfonates (1) are very photosensitive and easily undergo photodecomposition via initial homolysis of the Se-S bond.In the presence alkenes this facile photodissociation of 1 can be used to initiate a free radical chain reaction (eq 6) that leads to addition of 1 to the alkene to form β-phenylselenosulfones (2).The photoaddition requires much shorter reaction times than the non-photolytic addition of 1 to alkenes described recently.
- Gancarz, Roman A.,Kice, John L.
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- Radical Heck-type reaction of styrenes with sulfonyl hydrazides on water at room temperature
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Herein, metal-free radical Heck-type reaction of styrenes with sulfonyl hydrazides to synthesize vinyl sulfones is developed. The reaction is performed under economical TBAI/TBHP system on water in open air at room temperature, which proceeds through the
- Bao, Wen-Hui,Ying, Wei-Wei,Xu, Xu-Dong,Zhou, Guo-Dong,Meng, Xiao-Xiao,Wei, Wen-Ting,Liu, Yan-Yun,Li, Qiang
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- Alkyne-based, highly stereo- and regioselective synthesis of stereodefined functionalized vinyl tellurides
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(Z)-β-Aryltellurovinylphosphonates and (Z)-β-aryltellurovinyl sulfones were synthesized via the highly stereoselective anti-hydrotelluration of 1-alkynylphosphonates and 1-alkynyl sulfones. The configurations of these compounds were characterized via sup
- Huang,Liang,Xu,He
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- Photocatalytic radical cyclization of α-halo hydrazones with β-ketocarbonyls: Facile access to substituted dihydropyrazoles
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A mild and efficient method for the photocatalytic radical cyclization of α-halo hydrazones with β-ketocarbonyls has been described. This strategy provides a potential protocol for the construction of functionalized 4,5-dihydropyrazoles in moderate to high yields.
- Yu, Jing-Miao,Lu, Guo-Ping,Cai, Chun
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- One-pot approach for the regioselective synthesis of β-keto sulfones based on acid-catalyzed reaction of sulfonyl chlorides with arylacetylenes and water
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Reaction of sulfonyl chlorides with arylacetylenes and water in the presence of a catalytic amount of sulfonic acid in THF provided β-keto sulfones in good yields with excellent regioselectivity.
- Lai, Chunbo,Xi, Chanjuan,Jiang, Yanfeng,Hua, Ruimao
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- Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide
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A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is
- Ojha, Subhadra,Panda, Niranjan
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p. 1292 - 1298
(2022/02/19)
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- The Sulfinylsulfonation of alkynes for β-Sulfinyl alkenylsulfone
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Here we report the sulfinylsulfonation of alkynes to afford β-sulfinyl alkenylsulfone products with a broad substrate scope, excellent functional group compatibility, and high yield. Moreover, the sulfinylsulfonation reaction of enyne can also be realized for constructing functionalized carbo- and heterocycles through a radical cascade cyclization process.
- Feng, Chengjie,Ning, Yongquan,Song, Qingmin,Wang, Zikun,Wu, Yong,Zhang, Zhansong,Zhao, Wanjun
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(2022/05/23)
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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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- 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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- 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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- Dioxygen-Triggered Oxosulfonylation/Sulfonylation of Terminal Olefins toward β-Keto Sulfones/Sulfones
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A dioxygen-triggered oxosulfonylation/sulfonylation of unactivated olefins to achieve β-keto sulfones/sulfones has been developed. Interestingly, pluralistic mechanisms were found when different types of compounds were applied as substrates, and different products were achieved. The reaction is carried out with a high atomic efficiency in the absence of a metal and a catalyst at room temperature under an air atmosphere. Importantly, as a proof-of-concept, a bioactive molecule was synthesized on a gram-scale level using this method.
- Wang, Yanjie,Zhao, Yuhan,Cai, Changqun,Wang, Lingyun,Gong, Hang
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p. 8296 - 8301
(2021/11/13)
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- Copper-Catalyzed Heck-Type Couplings of Sulfonyl Chlorides with Olefins: Efficient and Rapid Access to Vinyl Sulfones
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A copper-catalyzed redox-neutral alkene sulfonylation reaction has been developed. This reported protocol can be easily scale up to a gram scale, and smoothly applied to the late-stage modification of several bioactive molecules.
- Chen, Qiulin,Liu, Lixia,Wang, Chengming,Xue, Pan
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supporting information
(2021/08/27)
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- Visible-light-induced surfactant-promoted sulfonylation of alkenes and alkynes with sulfonyl chloride by the formation of an EDA-complex with NaI in water at room temperature
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A green and efficient visible-light-induced iodosulfonyl reaction of alkenes in water using an EDA complex strategy at room temperature has been disclosed. The addition of a cationic surfactant allows for the easy formation of colored EDA complexes in water. The hydrophobic effect of the core in the surfactant aggregates, which act as a reaction medium formed by the surfactants themselves in water, plays a significant role in stabilizing the transition state and decreasing the activation energy of the reaction. Remarkably, transition-metal catalysts and organic solvents were not required in this transformation. Moreover, it displayed a broad substrate scope, good functional group tolerance, simple operation, scalability and high chemical selectivity. Thus, it not only provided a green and efficient synthetic strategy for the preparation of β-iodo-substituted sulfone derivatives, but also enriched the investigation of visible-light-induced reactions in water.
- Jiang, Hezhong,Li, Jiahong,Li, Jun-Long,Lin, Li,Liu, Jianchen,Liu, Xiang-Wei,Wang, Jingxia,Yang, Zhonglie,Zhang, Xiaobin,Zheng, Jiale
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supporting information
p. 5467 - 5473
(2021/08/16)
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- Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis
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An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.
- Cui, Wenwen,Jiang, Min,Lv, Jian,Song, Xiuyan,Sun, Kai,Xu, Guiyun,Yan, Qiuli,Yang, Daoshan
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p. 3663 - 3668
(2021/05/31)
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- Construction of 3-Sulfonyl Naphthalenes via Tandem Reaction of 1,4-Diyn-3-yl Esters with Sodium Sulfinates
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Polysubstituted 3-sulfonyl naphthalenes were constructed in good to high yields by AlCl3-mediated tandem reaction of 1,4-diyn-3-yl esters and sodium sulfinates. This reaction proceeded under mild reaction conditions and tolerated a variety of functional groups. Moreover, the mechanistic studies indicated that the initial formation of allene under DBU from 1,4-diyn-3-yl ester and a sequence of nucleophilic addition of sodium sulfinate, the formation of allene, and intramolecular cyclization might be involved.
- Guo, Ziyi,Zhao, Yiming,Wang, Yu,Xie, Meihua,Zhang, Jitan
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supporting information
p. 6247 - 6258
(2021/05/06)
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- 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
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supporting information
p. 7827 - 7831
(2021/09/28)
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- Electrochemical sulfonylation of alkenes with sulfonyl hydrazides: A metal- And oxidant-free protocol for the synthesis of (: E)-vinyl sulfones in water
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An efficient electrochemical transformation of a variety of alkenes and sulfonyl hydrazides into vinyl sulfones with a catalytic amount of tetrabutylammonium iodide in water is reported. The reaction proceeds smoothly to afford vinyl sulfones with good selectivities and yields at room temperature under air in an undivided cell. Cyclic voltammograms and control experiments have been performed to provide preliminary insight into the reaction mechanism. The key features of this reaction include using pure water as solvent, transition metal- and oxidant-free conditions, and being easily scaled up to gram-scale synthesis. This journal is
- Cai, Jianpeng,Guo, Huishi,Lai, Yin-Long,Liao, Jianhua,Luo, Jianmin,Mo, Yunyan,Yan, Shaoxi,Zhang, Shengling,Zhu, Lejie
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p. 33155 - 33160
(2020/10/05)
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- Electrochemical Synthesis of Vinyl Sulfones by Sulfonylation of Styrenes with a Catalytic Amount of Potassium Iodide
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An electrochemical sulfonylation reaction of styrenes was developed in which sodium arylsulfinates were used as sulfonylating reagents, a catalytic amount of KI was used as a redox mediator, and Bu 4NBF 4was used as the electrolyte. In addition to various styrenes, sodium arylsulfinates with either electron-donating or electron-withdrawing groups were tolerated.
- Wang, Pei-Long,Gao, Hui,Jiang, Zhi-Sheng,Li, Chao,Tian, Zhi-Ao,Li, Pin-Hua
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supporting information
p. 1720 - 1724
(2020/09/21)
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- Visible light promoted sulfonylation and sulfonylcarbonylation of alkenes
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Visible light promoted sulfonylation and sulfonylcarbonylation reactions of readily available alkenes with TosMIC for the synthesis of valuable vinyl sulfones and β-keto sulfones were described. A reasonable radical involved mechanism is proposed.
- Min, Wenjian,Guo, Guozhe,Yang, Caixia,Huo, Congde
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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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- 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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- Synthesis of vinyl sulfones through sulfonylation of styrenes with sulfonyl chlorides under metal-free conditions
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A hypervalent iodine reagent-mediated sulfonylation of styrenes with sulfonyl chlorides was developed for the synthesis of vinyl sulfones. The reaction proceeded under metal-free, mild and neutral conditions without extra oxidants or bases. It also exhibited good air and moisture tolerance, broad substrate scope and high chemo-selectivity, affording the vinyl sulfones in moderate to good yields.
- Hu, Bo,Li, Dong,Wang, Xia,Yang, Peng,Zhang, Qian
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- Silver-promoted synthesis of vinyl sulfones from vinyl bromides and sulfonyl hydrazides in water
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The synthesis of vinyl sulfones via silver-promoted cross-coupling of vinyl bromides with sulfonyl hydrazides was realized. Water was used as the sole solvent. Multisubstituted vinyl sulfones were easily prepared with excellent alkyl group tolerance. A mechanism involving nucleophilic attack of a sulfinate anion was proposed.
- Zhang, Ge,Fu, Jian-Guo,Zhao, Qian,Zhang, Gui-Shan,Li, Meng-Yao,Feng, Chen-Guo,Lin, Guo-Qiang
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supporting information
p. 4688 - 4691
(2020/05/22)
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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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- Copper-Catalyzed Disulfonation of Terminal Alkynes with Sodium Arylsulfinates
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A novel and direct disulfonylation reaction of commercially available terminal alkynes under copper(I)/bromodifluoroacetate cocatalyst has been realized. This protocol provides a facile and practical pathway to selectively access (E)-1,2-disulfonylethenes, in which features good functional group compatibility, easily available starting materials, and excellent stereoselectivity with good yields.
- Chen, Wanjiao,Gao, Wen,Liu, Zhenhua,Tang, Bo,Wang, Lianxiao,Yang, Lin,Yu, Tian,Zhang, Kaining
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supporting information
p. 2081 - 2086
(2020/03/24)
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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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- 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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- Visible-light-induced decarboxylative sulfonylation of cinnamic acids with sodium sulfinates by using Merrifield resin supported Rose Bengal as a catalyst
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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
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supporting information
p. 5578 - 5585
(2019/06/13)
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- Cu-doped zeolitic imidazolate framework catalysed highly selective conversion of alkynes to β -keto and vinyl sulfones using sodium sulfinates
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Abstract: Cu 2 +-doped zeolitic imidazolate framework-8 (ZIF-8)-catalyzed one-pot procedure to synthesize β -keto and vinyl sulfones by the direct oxysulfonylation and hydrosulfonylation of alkynes via radical reaction under mild conditions has been described. The advantages of this protocol included broad substrate scope and excellent β -keto and E-stereoselectivity. The Cu/ZIF-8 catalyst not only exhibited excellent performance but also had a great stability in the reaction, successfully allowing its reuse up to five cycles. This efficient Cu/ZIF-8 heterogeneous catalyst is explored for the first time to generate β -keto and vinyl sulfones. Graphical Abstract:: Cu 2 +-doped zeolitic imidazolate framework-8 (ZIF-8)-catalyzed one-pot procedure to synthesize β -keto and vinyl sulfones by the direct oxysulfonylation and hydrosulfonylation of alkynes via radical reaction under mild conditions is described. The advantages of this protocol included broad substrate scope and excellent β -keto and E-stereoselectivity. This efficient Cu/ZIF-8 heterogeneous catalyst is explored for the first time for C-S bond formation. [Figure not available: see fulltext.].
- Yalavarthi, Nageswara Rao,Gundoju, Narayanarao,Bokam, Ramesh,Ponnapalli, Mangala Gowri
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- A Study of Graphene-Based Copper Catalysts: Copper(I) Nanoplatelets for Batch and Continuous-Flow Applications
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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
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supporting information
p. 3011 - 3018
(2019/08/20)
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Based on the acid-base mixed-ligand assembly strategy, a stable Mn(II)-based metal-organic framework (denoted as Mn-MOFs), containing 1-D Mn–O–C rod-shaped chains, was hydrothermally synthesized and structurally characterized. This material was demonstrated to be an efficient heterogeneous catalyst for the decarboxylative sulfonylation of cinnamic acids with sodium benzene sulfinates. Moreover, the Mn-MOF catalyst could be recycled up to six times with the retention of both catalytic activity and crystal structure.
- Ding, Qi-Da,Si, Jin-Ping,Huang, Kun-Lin,Tian, Feng,Chen, Sheng-Chun,Feng, Xue-Jun,He, Ming-Yang,Chen, Qun
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- Visible-Light-Mediated Regioselective Chlorosulfonylation of Alkenes and Alkynes: Introducing the Cu(II) Complex [Cu(dap)Cl2] to Photochemical ATRA Reactions
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A visible-light-mediated photocatalyzed protocol utilizing copper-phenanthroline-based catalysts has been developed that can convert a large number of olefins into their chlorosulfonylated products. Besides the Cu(I) complex [Cu(dap)2]Cl, now well-established in photo-ATRA processes, the corresponding Cu(II) complex [Cu(dap)Cl2] proved to be often even more efficient in the title reaction, being advantageous from an economic point of view but also opening up new avenues for photoredox catalysis. Moreover, the copper complexes outperformed commonly used ruthenium, iridium, or organic dye based photocatalysts, owing to their ability to stabilize or interact with transient radicals by inner sphere mechanisms. The use of stoichiometric Na2CO3 in combination with the copper photocatalysts was found to be essential to convert unactivated olefins to the desired products, in contrast to activated olefins for which no additive was required. As suggested by appropriate control experiments, the role of Na2CO3 is attributed to prevention of poisoning of the catalyst.
- Hossain, Asik,Engl, Sebastian,Lutsker, Eugen,Reiser, Oliver
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p. 1103 - 1109
(2019/02/10)
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- (E)-(2-(phenylsulfonyl)vinyl)benzene and derivative thereof, and synthesis method of (E)-(2-(phenylsulfonyl)vinyl)benzene and derivative thereof
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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
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Paragraph 0054; 0057; 0058; 0059-0065; 0068; 0071
(2019/06/13)
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- TBN-mediated regio- and stereoselective sulfonylation & oximation (oximosulfonylation) of alkynes with sulfonyl hydrazines in EtOH/H2O
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An alkyne difunctionalization cascade reaction was developed to generate α-sulfonylethanone oximes under metal-free conditions. The reaction features environmentally benign EtOH/H2O as a solvent, a broad substrate scope and easily scaled up for gram-scale synthesis. The reaction mechanism was illustrated with UPLC, GC-MS and UPLC-tof/MS.
- Wang, Bin,Yan, Zicong,Liu, Liyan,Wang, Jiawei,Zha, Zhenggen,Wang, Zhiyong
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supporting information
p. 205 - 212
(2019/01/28)
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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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- Metal-free catalyzed synthesis of the (E)-vinyl sulfones via aromatic olefins with arylsulfonyl hydrazides
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Synthesis of vinyl sulfones from aromatic olefins and arylsulfonyl hydrazides via I2-TBHP catalyzed system under the N2 atmosphere is described. Owing to no use of metal, only producing N2 and water as the byproducts and d
- Zhan, Zhenzhen,Ma, Haojie,Wei, Daidong,Pu, Jinghong,Zhang, Yixin,Huang, Guosheng
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supporting information
p. 1446 - 1450
(2018/03/07)
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- Green preparation method for vinyl sulfone derivative in aqueous phase
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The invention relates to a green preparation method for a vinyl sulfone derivative in an aqueous phase. The method comprises the following steps: putting an olefin compound (1a), a sulfonyl hydrazidecompound of formula (2a) as shown in the specification, tetrabutylammonium iodide (TBAI), tert-butyl hydroperoxide (TBHP) and solvent water into a Schlenk reaction kettle, carrying out a stirring reaction on the reaction kettle at a certain temperature and an air atmosphere, monitoring the reaction process through TLC (Thin Layer Chromatography) or GC (Gas Chromatograph) till raw materials are completely reacted, and carrying out aftertreatment, thereby obtaining a target product, namely the vinyl sulfone derivative (I) as shown in the specification.
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Paragraph 0071-0073; 0083-0085
(2018/11/22)
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- E -Selective synthesis of vinyl sulfones via silver-catalyzed sulfonylation of styrenes
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An efficient and highly E-selective protocol for the synthesis of vinyl sulfones is described. This simple protocol demonstrates the first synthesis of vinyl sulfones via a silver-catalyzed C-S bond coupling reaction. In addition, the success of the reaction was found to be critically dependent on the use of TEMPO as the additive.
- Gui, Qingwen,Han, Kang,Liu, Zhuoliang,Su, Zhaohong,He, Xiaoli,Jiang, Hongmei,Tian, Bufan,Li, Yangyan
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supporting information
p. 5748 - 5751
(2018/08/21)
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- Gram-scale synthesis of β-sulfonyl styrenes
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A simple and gram-scale synthesis of β-sulfonyl styrenes has been developed starting from one-pot PPA (polyphosphoric acid)-catalyzed 1,1-diacetoxylation of arylacetaldehydes (ArCH2CHO) with acetic anhydride (Ac2O) followed by deacetoxylative sulfonylation of the resulting 1,1-diacetate intermediate with sodium sulfinates (RSO2Na) in good yields under solvent-free conditions.
- Chang, Meng-Yang,Wu, Yan-Shin,Hsiao, Yu-Ting
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p. 4651 - 4658
(2019/02/01)
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- Synthetic method of (E)-alkenyl sulfone compounds
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The invention discloses a synthetic method of (E)-alkenyl sulfone compounds. The method comprises the following steps: beta-nitroolefin compounds shown as formula I in the description, sulfohydrazidecompounds shown as formula II in the description, an iodine-containing nonmetal catalyst and a peroxide oxidizing agent are mixed for a reaction, and a mixture obtained after the reaction is subjectedto postprocessing, and the (E)-alkenyl sulfone compounds shown as formula III in the description are obtained. Beta-nitroolefin compounds, the sulfohydrazide compounds, the iodine-containing nonmetalcatalyst and the peroxide oxidizing agent are taken as main raw materials, the corresponding (E)-alkenyl sulfone compounds are synthesized through free radical reaction, the iodine-containing nonmetal catalyst iodine or tetrabutylammonium iodide is used, the raw materials are simple, easily available, cheap, non-toxic and pollution-free to the environment, the dosage of the catalyst is small, thecatalyst has higher specificity for the reaction, synthetic reaction time can be shortened, the problem that the metal catalyst is difficult to separate in the prior art can be well solved, postprocessing difficulty is reduced, yield of the final product is increased, and purity of the final product is improved.
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Paragraph 0040-0041; 0043
(2019/01/14)
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- Cross-Coupling of Sodium Sulfinates with Aryl, Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis
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An efficient photoredox/nickel catalyzed sulfonylation reaction of aryl, heteroaryl, and vinyl halides has been achieved for the first time. This newly developed sulfonylation protocol provides a versatile method for the synthesis of diverse aromatic sulfones at room temperature and shows excellent functional group tolerance. The electrophilic coupling partners are not limited to aryl, heteroaryl, and vinyl bromides and iodides, but also includes less reactive aryl chlorides as suitable substrates for this transformation.
- Yue, Huifeng,Zhu, Chen,Rueping, Magnus
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supporting information
p. 1371 - 1375
(2018/01/27)
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- A mild light-induced cleavage of the S-O bond of aryl sulfonate esters enables efficient sulfonylation of vinylarenes
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A new mode of S-O bond activation has been discovered, which constitutes novel reactivity of easily available and bench-stable arylsulfonate phenol esters. This protocol enables access to putative sulfonyl radical intermediates, which enable straightforward access to valuable vinyl sulfones.
- Ratushnyy, Maxim,Kamenova, Monika,Gevorgyan, Vladimir
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p. 7193 - 7197
(2018/10/02)
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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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- Electrochemical Decarboxylative Sulfonylation of Cinnamic Acids with Aromatic Sulfonylhydrazides to Vinyl Sulfones
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A stereoselective synthesis of (E)-vinyl sulfones has been developed via electrochemical oxidative N-S bond cleavage of aromatic sulfonylhydrazides, followed by cross-coupling reactions with cinnamic acids to form the C-S bond. The protocol proceeded smoo
- Zhao, Yu,Lai, Yin-Long,Du, Ke-Si,Lin, Dian-Zhao,Huang, Jing-Mei
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p. 9655 - 9661
(2017/09/23)
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- Copper(II)-Catalyzed Chemo- and Stereocontrolled Synthesis of (E)-Vinyl Sulfones and (Z)-β-Chlorovinyl Sulfones from Terminal Alkynes and Arylsulfonyl Hydrazides
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A facile copper(II)-catalyzed regio- and stereocontrolled synthesis of vinyl sulfones from terminal alkynes and arylsulfonyl hydrazides is described. Depending on the source of copper(II), two different kinds of vinyl sulfones, (E)-vinyl sulfones and (Z)-β-chlorovinyl sulfones were obtained and the addition of cyclohexanone played an important role in the reaction. These reactions display excellent chemoselectivity as well as stereoselectivity.
- Liu, Xiao-Tao,Ding, Zong-Cang,Ju, Lu-Chuan,Xu, Su-Xia,Zhan, Zhuang-Ping
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p. 1575 - 1582
(2017/03/21)
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- (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 0066-0069; 74-75
(2017/10/07)
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- Electrosynthesis of vinyl sulfones from alkenes and sulfonyl hydrazides mediated by KI: Аn electrochemical mechanistic study
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A variety of vinyl sulfones were prepared from alkenes and sulfonyl hydrazides via electrochemical oxidative sulfonylation. The reaction proceeds in an experimentally convenient undivided electrochemical cell equipped with graphite and iron electrodes employing KI as a redox catalyst and a supporting electrolyte. Applying extremely high current density up to 270 mA/cm2 permits rapid synthesis in a compact reactor and with small surface area electrodes. A possible reaction mechanism was proposed with the use of cyclic voltammetry. It is the combination of anodic and cathodic processes in this reaction that makes it possible to obtain products under mild conditions with yields from moderate to high.
- Terent'ev, Alexander O.,Mulina, Olga M.,Pirgach, Dmitry A.,Ilovaisky, Alexey I.,Syroeshkin, Mikhail A.,Kapustina, Nadezhda I.,Nikishin, Gennady I.
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p. 6871 - 6879
(2017/11/06)
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- Metal-free Oxidative Coupling of Aromatic Alkenes with Thiols Leading to (E)-Vinyl Sulfones
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A facile I2O5-mediated direct oxidative coupling of aromatic alkenes with thiols toward vinyl sulfones has been developed under metal-free conditions. This methodology provides a convenient and efficient approach to various (E)-vinyl sulfones from readily available starting materials with excellent regioselectivity. The present oxidative coupling reaction, not only expands the scope of functionalization of alkenes with thiols, but also makes it a practical and powerful complement to traditional methods for the synthesis of (E)-vinyl sulfones.
- Wang, Leilei,Yue, Huilan,Yang, Daoshan,Cui, Huanhuan,Zhu, Minghui,Wang, Jinming,Wei, Wei,Wang, Hua
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p. 6857 - 6864
(2017/07/17)
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- Base-mediated tandem sulfonylation and oximation of alkenes in water
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A base-mediated bifunctionalization of alkenes for the synthesis of α-sulfonylethanone oximes was developed in water under metal-free conditions. This reaction features a wide substrate scope and facile starting materials to afford the desired products in high yields.
- Wang, Bin,Tang, Lin,Liu, Liyan,Li, Yanan,Yang, Yu,Wang, Zhiyong
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supporting information
p. 5794 - 5799
(2017/12/26)
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- Synthesis of γ-sulfonyl δ-lactones and β-sulfonyl styrenes
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A facile route to the synthesis of γ-sulfonyl lactones 5 and β-sulfonyl styrenes 6 has been developed, achieving moderate to good yields via the (1) NaH mediated Michael addition of β-ketosulfones 3 and methyl acrylate in refluxing THF and (2) NaBH4mediated stereoselective reduction/lactonization of δ-ketoesters 4 in boiling MeOH, or (3) boron trifluoride etherate mediated ring-opening of lactones 5 in MeOH at reflux.
- Chan, Chieh-Kai,Chen, Yu-Hsin,Hsu, Ru-Ting,Chang, Meng-Yang
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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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- Iodine-Catalyzed Facile Approach to Sulfones Employing TosMIC as a Sulfonylating Agent
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A novel iodine-catalyzed functionalization of a variety of olefins and alkynes and direct decarboxylative functionalization of cinnamic and propiolic acids with TosMIC to provide access to various vinyl, allyl, and β-iodo vinylsulfones is described. This simple, efficient, and environmentally benign approach employing inexpensive molecular iodine as a catalyst demonstrates a versatile protocol for the synthesis of highly valuable sulfones, rendering it attractive to both synthetic and medicinal chemistry.
- Kadari, Lingaswamy,Palakodety, Radha Krishna,Yallapragada, Lakshmi Prapurna
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p. 2580 - 2583
(2017/05/24)
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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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