56480-95-6Relevant academic research and scientific papers
Synthesis of β-Keto Sulfones by Oxy-Sulfonylation of Alkynes in HFIP
Chen, Xingyu,Lu, Sixian,Zheng, Yuyan,Wang, Jigang,Yang, Lan,Sun, Peng
, p. 1305 - 1312 (2022/03/14)
Herein, we have established a method for the construction of β-keto sulfones through aerobic oxy-sulfonylation of alkynes with sulfinates. The reaction performed employing air as the oxidant and oxygen source. Moreover, this protocol exhibits low consume of sulfinates, short reaction period, and minimal waste. Mechanism study and density functional theory (DFT) calculation showed that the solvent played a significant role in the transformation. (Figure presented.).
Copper-catalyzed regioselective synthesis of (E)-β-fluorovinyl sulfones
Román, Raquel,Barrio, Pablo,Mateu, Natalia,Sedgwick, Daniel M.,Fustero, Santos
supporting information, (2019/05/02)
Organofluorine compounds are finding increasing application in a variety of fields such as pharmaceutical, agrochemical, and material sciences. However, given the scarcity of fluorine-containing natural products, advancement in this area depends almost entirely on the development of new synthetic methodologies. In this article, we present the synthesis of a series of previously undescribed (E)-β-fluorovinyl sulfones via a simple copper-catalyzed addition of hydrogen fluoride to alkynyl sulfone starting materials in varying yields and E/Z selectivities. The hydrogenation of these products was also explored and compared with the hydrogenation of the related Z isomers. These new products may find interesting applications, given the versatility of vinyl sulfones in chemical synthesis and the unique properties of vinyl fluorides in biological settings.
Radical Heck-type reaction of styrenes with sulfonyl hydrazides on water at room temperature
Bao, Wen-Hui,Ying, Wei-Wei,Xu, Xu-Dong,Zhou, Guo-Dong,Meng, Xiao-Xiao,Wei, Wen-Ting,Liu, Yan-Yun,Li, Qiang
supporting information, p. 55 - 58 (2018/11/30)
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
A metal-free and regioselective approach to (Z)-β-fluorovinyl sulfones and their chemoselective hydrogenation to β-fluoroalkyl sulfones
Sedgwick, Daniel M.,Román, Raquel,Barrio, Pablo,Morales, Cristina,Fustero, Santos
, p. 108 - 116 (2018/01/01)
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.
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
supporting information, p. 4205 - 4209 (2016/05/24)
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.
