100727-52-4Relevant academic research and scientific papers
Copper-Catalyzed Aerobic Oxidative Cleavage of Unstrained Carbon-Carbon Bonds of 1,1-Disubstituted Alkenes with Sulfonyl Hydrazides
Yi, Dong,He, Linying,Qi, Zhongyu,Zhang, Zhijie,Li, Mengshun,Lu, Ji,Wei, Jun,Du, Xi,Fu, Qiang,Wei, Siping
supporting information, p. 859 - 865 (2021/03/04)
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.
Synthesis method of beta-ketosulfone compound
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Paragraph 0055-0056; 0067-0069; 0072, (2020/05/08)
The invention discloses a synthesis method of a beta-ketosulfone compound, and belongs to the technical field of chemical synthesis. According to the synthesis method, tetrafluoroborate diazonium salt, alkyne and DABCO. (SO2) 2 are subjected to an oxidation bifunctionalization reaction to prepare the beta-ketosulfone compound. The method comprises the following steps: adding DABCO.( SO2) 2, alkyneand tetrafluoroborate diazonium salt which are used as reactants and mesoporous carbon nitride, an organic solvent, water and oxygen which are used as catalysts into a reactor, and stirring for 6-10hours at room temperature under the irradiation of visible light. The method is mild in reaction condition, simple to operate and high in atom economy, and the catalysts can be recycled.
Preparation method of beta-carbonyl sulfone compound
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Paragraph 0039-0042; 0143-0146, (2020/12/09)
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.
Heterogeneous Carbon Nitrides Photocatalysis Multicomponent Hydrosulfonylation of Alkynes to Access β-Keto Sulfones with the Insertion of Sulfur Dioxide in Aerobic Aqueous Medium
Ni, Bangqing,Zhang, Binbin,Han, Jine,Peng, Bohan,Shan, Yuling,Niu, Tengfei
supporting information, p. 670 - 674 (2020/01/31)
Although hydrosulfonylation of alkynes is an ideal process to generate β-keto sulfones, such an approach is rarely implemented. Here we reported a facile and efficient graphitic carbon nitride (p-g-C3N4) photocatalyzed hydrosulfonylation of alkynes with the insertion of sulfur dioxide in aerobic conditions. Controlled experiments and ESR results indicated both the superoxide radicals and valence band holes played an important role in the reaction. Further isotope experiments confirmed the oxygen atom of the products comes from H2O, while the O2 plays an important role in the reaction by quenching the DABCO radical cation. The metal-free heterogeneous semiconductor is fully recyclable at least 6 times without significant reducing activity. Furthermore, this reaction could be carried out under solar light irradiation and was applicable for a large-scale reaction with conserved results.
Synthesis of β-Keto Sulfones via Coupling of Aryl/Alkyl Halides, Sulfur Dioxide and Silyl Enolates through Metal-Free Photoinduced C–X Bond Dissociation
Gong, Xinxing,Ding, Yechun,Fan, Xiaona,Wu, Jie
supporting information, p. 2999 - 3004 (2017/09/08)
A photoinduced sulfonylative coupling of aryl/alkyl halides, DABCO?(SO2)2 (1,4-diazabicyclo[2.2.2]octane-sulfur dioxide), and silyl enolates under metal-free conditions has been developed, giving rise to β-keto sulfones in good yields. This transformation proceeds smoothly at room temperature under ultraviolet irradiation with good tolerance of various functional groups. Aryl iodides/bromides and alkyl halides are all good substrates in the sulfonylative reaction. A plausible mechanism is proposed, which proceeds through a radical process under photoinduced conditions. (Figure presented.).
Visible-light-promoted oxidative difunctionalization of alkenes with sulfonyl chlorides to access β-keto sulfones under aerobic conditions
Niu, Teng-fei,Cheng, Jing,Zhuo, Chang-li,Jiang, Ding-yun,Shu, Xing-ge,Ni, Bang-qing
supporting information, p. 3667 - 3671 (2017/08/22)
A mild, practical and efficient strategy to prepare β-keto sulfones has been developed by visible light promoted reactions. This reaction involves Ir(ppy)2(dtbbpy)PF6 catalyzed direct funcationalization of alkenes with sulfonyl chlorides under mild conditions. Air was used as oxidant without any additives. The transformation affords the corresponding products in moderate to high yields.
Visible-light-induced direct oxysulfonylation of alkynes with sulfonyl chlorides and HCl
Niu, Tengfei,Jiang, Dingyun,Ni, Bangqing
supporting information, p. 4299 - 4303 (2017/10/12)
A mild, practical and efficient strategy to prepare β-keto sulfones has been developed by visible-light-induced reactions. This reaction involved Ir(dtbbpy)(ppy)2PF6-catalyzed direct functionalization of alkynes with sulfonyl chloride and HCl using air as the oxidant. HCl not only acted as a hydrogen source in the proton transfer process, but also played a vital role in the reaction process.
Sulfonation and trifluoromethylation of enol acetates with sulfonyl chlorides using visible-light photoredox catalysis
Jiang, Heng,Cheng, Yuanzheng,Zhang, Yan,Yu, Shouyun
supporting information, p. 5485 - 5492 (2013/09/02)
A mild, practical method to prepare α-sulfonyl and α-trifluoromethyl ketones from readily available enol acetates and sulfonyl chlorides has been developed using visible-light photoredox catalysis. The method could be used with a wide range of enol acetates and sulfonyl chlorides, and gave the desired products in satisfactory to excellent yields. A practical method to prepare α-sulfonyl and α-trifluoromethyl ketones from enol acetates and sulfonyl chlorides using visible-light photoredox catalysis is presented. Copyright
