86516-51-0Relevant articles and documents
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.
Dioxygen-Triggered Oxosulfonylation/Sulfonylation of Terminal Olefins toward β-Keto Sulfones/Sulfones
Wang, Yanjie,Zhao, Yuhan,Cai, Changqun,Wang, Lingyun,Gong, Hang
supporting information, p. 8296 - 8301 (2021/11/13)
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.
Electrochemical Sulfonylation of Alkynes with Sulfonyl Hydrazides: A Metal- and Oxidant-Free Protocol for the Synthesis of Alkynyl Sulfones
Mo, Zu-Yu,Zhang, Yu-Zhen,Huang, Guo-Bao,Wang, Xin-Yu,Pan, Ying-Ming,Tang, Hai-Tao
, p. 2160 - 2167 (2020/03/04)
Herein, an electrochemical oxidative cross-coupling reaction between terminal alkynes and sulfonylhydrazides has been developed. Tetrabutylammonium iodide is used as the electrolyte and redox medium. The significant advantages of this method are high atom efficiency, functional group tolerance, and transition metal- and oxidant-free conditions. Most of the compounds exhibit good inhibitory activity on tumor cell lines, and one of the compounds can inhibit cell migration and induce apoptosis in HeLa cells. (Figure presented.).
