86358-30-7Relevant articles and documents
Electrochemical two-electron oxygen reduction reaction (ORR) induced aerobic oxidation of α-diazoesters
Chen, Liang,Gao, Meng,Lu, Cuifen,Ma, Chao,Ruan, Mengyao,Wen, Ziyang,Yang, Fan,Yang, Guichun
, p. 2168 - 2171 (2022/02/17)
Electrochemical oxygen reduction reaction (ORR) is a powerful tool for introducing oxygen functional groups in synthetic chemistry. However, compared with the well-developed one-electron oxygen reduction process, the applications of two-electron oxygen re
Metal-Free Oxidative Esterification of Ketones and Potassium Xanthates: Selective Synthesis of α-Ketoesters and Esters
Luo, Xianglin,He, Runfa,Liu, Qiang,Gao, Yanping,Li, Jingqing,Chen, Xiuwen,Zhu, Zhongzhi,Huang, Yubing,Li, Yibiao
, p. 5220 - 5230 (2020/05/18)
A novel and efficient oxidative esterification for the selective synthesis of α-ketoesters and esters has been developed under metal-free conditions. In the protocol, various α-ketoesters and esters are available in high yields from commercially available ketones and potassium xanthates. Mechanistic studies have proven that potassium xanthate not only promotes oxidative esterification but also provides an alkoxy moiety for the reaction, which involves the cleavage and reconstruction of C-O bonds.
Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation
Xie, Shasha,Li, Defang,Huang, Hanchu,Zhang, Fuyuan,Chen, Yiyun
supporting information, p. 16237 - 16242 (2019/10/14)
The intermolecular radical addition to the carbonyl group is difficult due to the facile fragmentation of the resulting alkoxyl radical. To date, the intermolecular radical addition to ketones, a valuable approach to construct quaternary carbon centers, remains a formidable synthetic challenge. Here, we report the first visible-light-induced intermolecular alkyl boronic acid addition to α-ketoacids enabled by the Lewis acid activation. The in situ boron complex formation is confirmed by various spectroscopic measurements and mechanistic probing experiments, which facilitates various alkyl boronic acid addition to the carbonyl group and prevents the cleavage of the newly formed C-C bond. Diversely substituted lactates can be synthesized from readily available alkyl boronic acids and ketoacids at room temperature merely under visible light irradiation, without any additional reagent. This boron activation approach can be extended to alkyl dihydropyridines as radical precursors with external boron reagents for primary, secondary, and tertiary alkyl radical additions. The pharmaceutically useful anticholinergic precursors are easily scaled up in multigrams under metal-free conditions in flow reactors.
