- Method for synthesizing beta-ketosulfone derivative under mild condition and obtained beta-ketosulfone derivative
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The invention discloses a method for synthesizing a beta-ketosulfone derivative under a mild condition, which comprises the following steps: dissolving aryl olefin and sodium sulfinate in a solvent in a reaction container, adding an acidic additive, sealing the reaction container under the conditions that air exists in the reaction container and no transition metal exists, and purifying after reaction to obtain the beta-ketosulfone derivative. The free radical addition oxidation reaction of olefin and sulfinic acid can be realized under the mild condition without transition metal, the reaction raw materials are cheap and easy to obtain, no organic metal reagent or transition metal is needed, air is used as an oxidizing agent, no dangerous peroxide or persulfide is needed, and the method is compatible with air. The method has the advantages of simple operation and the like, and overcomes the defects of transition metal participation, large catalyst consumption, expensive reagents, high method cost, more reaction steps, more by-products and the like in the prior art.
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Paragraph 0064; 0065
(2021/08/28)
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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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supporting information
p. 8296 - 8301
(2021/11/13)
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- Copper-Catalyzed Aerobic Oxidative Cleavage of Unstrained Carbon-Carbon Bonds of 1,1-Disubstituted Alkenes with Sulfonyl Hydrazides
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Alkoxy radical-mediated carbon-carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic-type transformations. However, carbon-carbon cleavage reaction triggered by alkoxy radical intermediate derived from the combination of alkyl radical and dioxygen, is scarce and underdeveloped. Herein, we report alkoxy radical, which was generated from alkyl radical and dioxygen, mediated selective cleavage of unstrained carbon-carbon bond for the oxysulfonylation of 1,1-disubstituted alkenes, providing facile access to a variety of valuable β-keto sulfones. Mechanistic experiments indicated alkoxy radical intermediate that underwent subsequent regioselective β-scission might be involved in the reaction and preliminary computational studies were conducted to provide a detailed explanation on the regioselectivity of the C—C bond cleavage. Notably, the strategy was successfully applied for constructing uneasily obtained architecturally intriguing molecules.
- Yi, Dong,He, Linying,Qi, Zhongyu,Zhang, Zhijie,Li, Mengshun,Lu, Ji,Wei, Jun,Du, Xi,Fu, Qiang,Wei, Siping
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supporting information
p. 859 - 865
(2021/03/04)
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- Preparation method of beta-carbonyl sulfone compound
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The invention discloses a preparation method of a beta-carbonyl sulfone compound, and belongs to the technical field of organic synthesis. The preparation method of the beta-carbonyl sulfone compoundis provided for solving the problems that in the prior art, operation is complex, the substrate range is narrow, and the functional group tolerance is poor. The preparation method comprises the stepsof taking a compound shown in formula I and a compound shown in formula II as raw materials, taking copper salt as a catalyst, carrying out reaction in an organic solvent, and after the reaction is completed, carrying out aftertreatment to obtain the beta-carbonyl sulfone compound. The preparation method is simple and convenient to operate, mild in reaction condition, wide in substrate range and good in functional group tolerance, the yield reaches up to 93%, and the synthesis cost is remarkably reduced.
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Paragraph 0039-0042; 0047-0050
(2020/12/09)
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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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supporting information
(2020/05/26)
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- Synthesis of β-ketosulfone derivatives as new non-cytotoxic urease inhibitors in vitro
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Background: Peptic ulcer and urolithiasis are largely due to infection caused by urease-producing bacteria. Therefore, the discovery of urease inhibitors is an important area of medicinal chemistry research. Objective: The main aim of the work was to identify novel urease inhibitors with no cytotoxicity. Method: During the current study, a series of β-ketosulfones 1-26 was synthesized in two steps and evaluated for their in vitro urease inhibition potential. Results: Out of twenty-six compounds, seventeen have shown good to significant urease inhibitory activity with IC50 values ranging between 49.93-351.46 μM, in comparison to standard thiourea (IC50 = 21 ± 0.11 μM). Moreover, all compounds found to be non-cytotoxic against normal 3T3 cell line. Conclusion: This study has identified β-ketosulfones as novel and non-cytotoxic urease inhibitors.
- Iqbal Choudhary, M.,Iqbal, Sarosh,Khan, Ajmal,Khan, Khalid Mohammed,Kiran, Shumaila,Nazir, Rashid,Perveen, Shahnaz
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p. 244 - 255
(2020/03/10)
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- One-pot synthesis of β-ketosulfones from sulfonyl chloride, hydrazine hydrate and vinyl azide in water
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A novel, facile and efficient strategy for the one-pot synthesis of β-ketosulfones from readily available sulfonyl chloride, hydrazine hydrate and vinyl azides is described. The reaction proceeded very smoothly affording diverse β-ketosulfones in moderate to good yields. This new procedure has the advantages of environmental benign, easy and simple operation, low cost and wide tolerance of functional groups, which provides a highly fascinating protocol to access β-ketosulfones.
- Zhang, Yaohong,Luo, Mengqiang,Li, Yan,Shen, Runfu,Qi, Chenze,Wang, Hai,Cheng, Kai
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supporting information
(2020/10/26)
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- Method for synthesizing alpha-sulfone ketone compound from alpha, alpha-dibromo ketone by one-pot process
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The invention discloses a method for synthesizing a high-added-value alpha-sulfone ketone compound from an alpha, alpha-dibromo ketone compound by a one-pot process. The method has the advantages thatan alpha-sulfone ketone derivative is synthesized from alpha, alpha-dibromo ketone, which is simple and easy to obtain, by the one-pot process without separation of an alpha-bromo ketone intermediate, so that a separation process for an intermediate product is omitted, the steps are reduced, and requirements for environment protection are met; the steps of the method are simple and easy to operate, no transition metal reagents are required, and economical sulfonate with less pollution is directly used as a promoter and a sulfonating agent for reducing debromination of the alpha, alpha-dibromoketone, so that the cost is reduced, and economic benefits of reactions are increased; a system for preparing the alpha-sulfone ketone derivative by the one-pot process is developed to provide a novel synthesis method for preparation of the alpha-sulfone ketone compound, and the method has good industrialization prospect and potential application value.
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Page/Page column 11; 12
(2019/10/17)
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- A metal-free and regioselective approach to (Z)-β-fluorovinyl sulfones and their chemoselective hydrogenation to β-fluoroalkyl sulfones
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A highly regioselective, metal-free hydrofluorination reaction of alkynyl sulfones was developed using TBAF—one of the cheapest and most commonly available fluoride sources. In addition, the reactivity of the resulting β-fluorovinyl sulfones was studied, focusing on their selective hydrogenation reaction. Both β-fluorovinyl sulfones and their hydrogenation products β-fluoroalkyl sulfones may find applications in medicinal and agrochemical sciences.
- Sedgwick, Daniel M.,Román, Raquel,Barrio, Pablo,Morales, Cristina,Fustero, Santos
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p. 108 - 116
(2018/01/01)
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- Regiocontrolled synthesis of α-sulfonylmethyl o-nitrostyrenes via ZnI2-mediated sulfonylation and AgNO2/Pd(PPh3)4-promoted o-nitration
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We report herein the AgNO2/Pd(PPh3)4-promoted regiocontrolled o-nitration of α-sulfonylmethylstyrenes in MeNO2 with good yields. The o-nitration process provides a series of sulfonyl o-nitrostyrenes. Substituted α-sulfonylmethylstyrenes were synthesized from ZnI2-mediated sulfonylation of substituted α-methylstyrenes and sodium sulfinates (RSO2Na) in MeCN with good to excellent yields. The structures of the key products were confirmed by X-ray crystallography. A plausible mechanism has been proposed herein.
- Chang, Meng-Yang,Chen, Han-Yu,Wang, Heui-Sin
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p. 10601 - 10610
(2018/05/31)
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- Copper Triflate Mediated α-Monohalogenation of α-Diazo β-Ketosulfones with Ammonium Halides
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Copper triflate mediated α-monohalogenation of α-diazo β-ketosulfones with ammonium halides provides the corresponding α-halo β-ketosulfones. Different metal triflates are investigated for this facile and efficient transformation. A plausible mechanism is proposed.
- Chan, Chieh-Kai,Wang, Heui-Sin,Hsu, Ru-Ting,Chang, Meng-Yang
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p. 2045 - 2056
(2017/04/26)
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- Construction of Sulfonyl Oxabenzo[3.3.1]bicyclic Core via Cyclocondensation of β-Ketosulfones and o-Formyl Allylbenzenes
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NH4OAc mediated domino Knoevenagel/Diels-Alder cyclocondensation of β-ketosulfones 1 and o-formyl allylbenzenes 2 provides sulfonyl oxabenzo[3.3.1]bicyclic core 4 in a cosolvent of toluene and HOAc (v/v = 1/1) at reflux for 3 h. The intermediate 3 contains a chalcone motif. The uses of various ammonium salts and solvent systems are investigated for facile and efficient transformation. The plausible mechanisms have been proposed and the DFT calculations have been included.
- Hsueh, Nai-Chen,Chen, Hsing-Yin,Chang, Meng-Yang
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p. 13324 - 13332
(2017/12/26)
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- Synthesis of (E)-1,4-diaryl-2-butene-1,4-diones
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We report a facile route for the preparation of symmetric and unsymmetric (E)-1,4-diaryl-2-butene-1,4-diones 3 by a two-step route, including (1) nucleophilic substitution of 1 with sulfinic acid sodium salts, and (2) K2CO3 mediated alkylation of β-ketosulfones 4 with 1 followed by sequential desulfonylation of the resulting 1,4-diketones 5 in acetone. These products were obtained in high yields.
- Chan, Chieh-Kai,Chang, Meng-Yang
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p. 390 - 405
(2017/01/29)
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- Synthesis of 2-arylbenzimidazole analogues
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Substituted 2-arylbenzimidazoles (4) were easily synthesized in good yields starting from the condensation reaction of 1,2-diaminobenzenes (1) with β-ketosulfones (5) in the presence of boiling HOAc.
- Chang, Meng-Yang,Chan, Chieh-Kai,Chen, Yi-Chia
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p. 1229 - 1236
(2014/05/20)
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- Aerobic oxidation in nanomicelles of aryl alkynes, in water at room temperature
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On the basis of the far higher solubility of oxygen gas inside the hydrocarbon core of nanomicelles, metal and peroxide free aerobic oxidation of aryl alkynes to β-ketosulfones has been achieved in water at room temperature. Many examples are offered that illustrate broad functional group tolerance. The overall process is environmentally friendly, documented by the associated low E Factors. It's all happenin' in the micelle! The highly preferential dissolution of oxygen gas within the lipophilic cores inside nanomicelles leads to efficient trapping of in situ generated vinyl radicals. These intermediate radicals, derived from arylalkynes and sulfinic acids, lead to β-ketosulfone products, formed under especially mild and green conditions: no metals, no heating or cooling, recyclable aqueous media, and low E Factors.
- Handa, Sachin,Fennewald, James C.,Lipshutz, Bruce H.
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p. 3432 - 3435
(2014/04/03)
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