1492822-28-2Relevant academic research and scientific papers
Visible-light-promoted syntheses of β-keto sulfones from alkynes and sulfonylhydrazides
Cai, Shunyou,Chen, Danling,Xu, Yaohui,Weng, Wen,Li, Lihuang,Zhang, Ruijie,Huang, Mingqiang
, p. 4205 - 4209 (2016)
A variety of functionalized β-keto sulfones were smoothly prepared through oxysulfonylation of commercially available alkynes with sulfonylhydrazides under the synergistic interactions of visible light irradiation, Ru(bpy)3Cl2 photocatalyst, oxygen, KI, and NaOAc basic additive under very mild reaction conditions.
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.
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.
Photoinduced rearrangement of vinyl tosylates to β-ketosulfones
Xie, Lili,Zhen, Xiaomeng,Huang, Shuping,Su, Xiaolong,Lin, Mai,Li, Yi
, p. 3530 - 3534 (2017/08/15)
We developed a photoinduced radical fragmentation and rearrangement of vinyl tosylates that enables efficient formation of β-ketosulfones. This process is based on the photoinitiated homolysis of vinyl tosylate to release a sulfinyl radical from the tosyl group and the subsequent addition of a sulfinyl radical to another vinyl tosylate to form the desired β-ketosulfones. This simple protocol features a broad scope with both aromatic and aliphatic substrates, convenient reagents and operating systems.
Copper-catalyzed coupling of oxime acetates with sodium sulfinates: An efficient synthesis of sulfone derivatives
Tang, Xiaodong,Huang, Liangbin,Xu, Yanli,Yang, Jidan,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 4205 - 4208 (2014/05/06)
Sulfone derivatives are important synthetic intermediates. However, the general method for their preparation is through traditional coupling reaction: the alkylation of sodium sulfinates with phenacyl halides. Based on our previous work on sodium sulfinates and oxime acetates, we herein report a novel method for sulfone derivatives by oxidative coupling with sodium sulfinates and oxime acetates using copper as catalyst. The sulfonylvinylamine products could be formed in excellent yields. Upon hydrolysis by silica gel in CH 2Cl2, β-ketosulfones could also be efficiently constructed. Various sulfonylvinylamines and β-ketosulfones were obtained in good to excellent yields under the optimized reaction conditions. Mechanistic studies indicated that this transformation involved copper-catalyzed N-O bond cleavage, activation of a vinyl sp2 C-H bond, and C-S bond formation. The oxime acetates act as both a substrate and an oxidant, thus the reaction needs no additional oxidants or additives. Copper brings us together: The title reaction involves copper-catalyzed N-O bond cleavage, activation of a vinyl sp2 C-H bond and C-S bond formation; it uses simple oxime acetates and sodium sulfinates to synthesize sulfonylvinylamine products without the need for additional oxidants or additives. Upon hydrolysis, useful β-ketosulfones are obtained.
