694500-60-2Relevant academic research and scientific papers
Oxidant-free C-H sulfonylation of enamides: Electrochemical synthesis of β-amidovinyl and carbonyl sulfones from sulfonyl hydrazide and enamides
Qi, Liang,Xiao, Linxia,Chen, Xi,Zhang, Ziyi,Shi, Qin,Chen, Jinkang
supporting information, (2021/12/17)
A mild, practical, eco-friendly and environmentally friendly electrochemical synthesis method of β-aminovinyl sulfone and carbonyl sulfones from sulfonyl hydrazide and enamides has been developed. This transformation only requires electrolytes and solvent, thus avoids transition metal catalysts, stoichiometric oxidant and base. Two different types of sulfone derivatives can be obtained only by changing the reaction solvent. This transformation also features mild conditions (room temperature, air), broad substrate scopes, and excellent stereoselectivities in mild to good yield.
Cu(OTf)2-Catalyzed efficient sulfonylation of vinyl azides with sodium sulfinates
Ning, Zhitao,Xu, Zheng,Liu, Ruikai,Du, Zhengyin
supporting information, p. 3492 - 3500 (2021/10/14)
A simple oxidative cross-coupling reaction between vinyl azides and sodium sulfinates was developed. This reaction uses commercial arylsulfinates that are more efficient, cheaper, and more stable as sulfonylation reagents, for efficiently, cheaply, and environmentally friendly synthesis of β-keto sulfones. And the reaction has the advantages of simple operation, high efficiency, good yield, and also has a wide range of functional group tolerance.
Photosensitizer-free synthesis of β-keto sulfones: Via visible-light-induced oxysulfonylation of alkenes with sulfonic acids
Hong, Yun-Yun,Peng, Sha,Peng, Zhen,Tang, Shan-Shan,Xie, Long-Yong,Xu, Xiang-Qun,Yang, Li-Hua
supporting information, p. 4537 - 4541 (2021/05/31)
A practical and environment-friendly methodology for the construction of β-keto sulfones through visible-light induced direct oxysulfonylation of alkenes with sulfonic acids at ambient temperature under open-air conditions was developed. Most importantly, the reaction proceeded smoothly without the addition of any photocatalyst or strong oxidant, ultimately minimizing the production of chemical waste.
Metal-Free Electrochemical Coupling of Vinyl Azides: Synthesis of Phenanthridines and β-Ketosulfones
Chen, Qianjin,Kong, Xianqiang,Li, Guodong,Liang, Qi,Lin, Long,Xu, Bo,Yu, Ke
, p. 6135 - 6145 (2020/10/06)
We reported an efficient and environmentally benign electrochemical synthesis of phenanthridines by oxidative coupling of vinyl azides with sodium azide or benzenesulfonyl hydrazides, for the first time. The reaction conditions are mild, and no additional metal-catalyst or exogenous oxidants are needed. The protocol has broad substrate scope and high functional group tolerance. Furthermore, this green electrochemical procedure can be readily extended to the synthesis of β-ketosulfones. Gram scale reactions further demonstrate the practicability.
Preparation method of oxalyl sulfonyl hydrazide and application of oxalyl sulfonyl hydrazide in olefin sulfonation reaction
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Paragraph 0025; 0028-0029, (2019/05/28)
The invention belongs to the technical field of organic chemical synthesis and particularly relates to a preparation method of oxalyl sulfonyl hydrazide and application of the oxalyl sulfonyl hydrazide in olefin sulfonation reaction. The preparation metho
Method for preparing beta-keto sulfone or beta-hydroxy sulfone from reaction of substituted olefin and sulfonyl hydrazine derivative
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Paragraph 0017; 0018; 0021; 0022, (2019/02/06)
The invention belongs to the technical field of organic chemical synthesis and specifically relates to a method for preparing beta-keto sulfone or beta-hydroxy sulfone from reaction of substituted olefin and sulfonyl hydrazine derivative. The method comprises the following steps: taking substituted olefin and sulfonyl hydrazine derivative as raw materials, taking air as an oxidizing agent and performing oxidizing addition reaction under the existence of photosensitizer and alkali and under the condition of visible light irradiation, thereby generating beta-keto sulfone or beta-hydroxy sulfone.The method provided by the invention is low in cost of raw materials, simple in process, green and safe, efficient and environment-friendly, and suitable for industrial production.
Heterogeneous copper-catalyzed oxidative coupling of oxime acetates with sodium sulfinates: An efficient and practical synthesis of β-keto sulfones
Xia, Jianhui,Huang, Xue,You, Shengyong,Cai, Mingzhong
, (2019/06/08)
An efficient and practical route to β-keto sulfones has been developed through heterogeneous oxidative coupling of oxime acetates with sodium sulfinates by using an MCM-41-supported Schiff base-pyridine bidentate copper (II) complex [MCM-41-Sb,Py-Cu (OAc)2] as the catalyst and oxime acetates as an internal oxidant, followed by hydrolysis. The reaction generates a variety of β-keto sulfones in good to excellent yields. This new heterogeneous copper (II) catalyst can be easily prepared via a simple procedure from readily available and inexpensive reagents and exhibits the same catalytic activity as Cu (OAc)2. MCM-41-Sb,Py-Cu (OAc)2 is also easy to recover and is recyclable up to eight times with almost consistent activity.
Visible-light promoted aerobic difunctionalization of alkenes with sulfonyl hydrazides for the synthesis of β-keto/hydroxyl sulfones
Wu, Jie,Zhang, Yulan,Gong, Xinchi,Meng, Yunge,Zhu, Chunyin
supporting information, p. 3507 - 3513 (2019/04/14)
A practical method has been developed for the conversion of alkenes to β-keto/hydroxyl sulfones by their reaction with sulfonyl hydrazides under metal-free conditions. This reaction proceeds through the oxidative addition of alkenes by sulfonyl radicals that are generated by visible-light induced oxidation of sulfonyl hydrazides. Notaly the reaction uses O2 as the terminal oxidant, instead of metal catalysts or oxidants like TBHP, leading to H2O and N2 as the clean by-products. The key features of this reaction include readily available reagents, mild reaction conditions and broad substrate scope.
Metal-free TBAI-catalyzed oxidative Csp3–S bond formation through Csp2–Csp2 bond and S–N bond cleavage: A new route to β-keto-Sulfones
Tang, Yucai,Chen, Ying,Liu, Hui,Guo, Min
supporting information, p. 3703 - 3705 (2018/09/14)
A novel TBAI-catalyzed radical sulfonylation of readily available N,N-dimethylenaminones with sulfonylhydrazides to afford functionalized β-keto-sulfones has been developed. Various functional groups were tolerated well under the present oxidative conditions and the corresponding β-keto-sulfone compounds were obtained in moderate to good yields. Importantly, this transformation offered the first protocol for Csp3–S bond formation by oxidative Csp2–Csp2 bond cleavage in one step.
Synthesizing method of beta-keto sulfone compound
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Paragraph 0064; 0065; 0067, (2018/09/08)
The invention discloses a synthesizing method of a beta-keto sulfone compound. The synthesizing method includes: mixing a compound I as shown in formula I and a compound II as shown in formula II withan oxidizing agent to obtain mixed liquid, and adding a copper catalyst into the mixed liquid by three times; sequentially subjecting the mixture obtained after the reaction to cation exchange membrane processing and post-processing to obtain the beta-keto sulfone compound as shown in formula III. The synthesizing method has the advantages that the compound I is used as the raw material, the rawmaterial is simple and easy to obtain, the synthesizing route is simple, side reaction is reduced, and high product purity and yield are achieved; the used copper catalyst is cheap and has high specificity to the reaction of the method, the copper catalyst is added by three times and coordinated with the other raw materials, the mixture obtained after the reaction is sequentially subjected to cation exchange membrane processing and post-processing, and the problem that a metal catalyst is hard to separate in the prior art can be well solved.
