Han Xiao-Wei, He Yuan, Gui Chao, Chu Xue-Qiang, Zhao Xue-Fei, Hu Xu-Hong, Zhou Xiaocong, Rao Weidong, Shen Zhi-Liang
Technical Institute of Fluorochemistry (TIF), School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
College of Biological, Chemical Science and Engineering, Jiaxing University, 118 Jiahang Road, Jiaxing 314001, China.
J Org Chem. 2024 Sep 20;89(18):13661-13668. doi: 10.1021/acs.joc.4c01851. Epub 2024 Sep 9.
Aryl 2-pyridyl esters could efficiently undergo cross-electrophile couplings with aryl bromides with the aid of magnesium as a reducing metal in the absence of a transition-metal catalyst, leading to the unsymmetrical diaryl ketones in modest to good yields with wide functionality compatibility. In addition, the reaction could be easily scaled up and applied in the late-stage modification of biologically active molecules. Preliminary mechanistic study showed that the coupling reaction presumably proceeds through the in situ formation of arylmagnesium reagents as key intermediates.
在没有过渡金属催化剂的情况下,芳基2-吡啶酯在镁作为还原金属的帮助下能与芳基溴有效地进行交叉亲电偶联反应,以中等至良好的产率生成具有广泛官能团兼容性的不对称二芳基酮。此外,该反应易于放大规模,并可应用于生物活性分子的后期修饰。初步机理研究表明,该偶联反应可能通过原位形成芳基镁试剂作为关键中间体进行。