Yao Jiaxin, Xiao Yuxuan, Li Haiyan, Yang Xun, Du Jiahui, Yin Ying, Feng Lin, Duan Wengui, Yu Lin
School of Chemistry and Chemical Engineering, Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, Guangxi University, Nanning 530004, Guangxi, P. R. China.
Org Lett. 2024 Sep 6;26(35):7307-7312. doi: 10.1021/acs.orglett.4c02340. Epub 2024 Aug 22.
A general approach for the α-arylation of heteroarenes with nitroarenes via denitrative coupling is reported for the first time. Various heteroarenes, including derivatives of furan, benzofuran, pyrrole, indole, thiophene, and benzothiophene, can be arylated at the α-position in moderate to good yields. Mechanistic studies demonstrate that the reaction proceeds via a CMD pathway, with C-H bond activation as the rate-determining step. Furthermore, the scalability and applicability in the synthesis of a drug molecule exemplify the utility of this protocol.
首次报道了一种通过脱硝基偶联实现杂芳烃与硝基芳烃α-芳基化的通用方法。各种杂芳烃，包括呋喃、苯并呋喃、吡咯、吲哚、噻吩和苯并噻吩的衍生物，都可以在α位进行芳基化，产率中等至良好。机理研究表明，该反应通过CMD途径进行，其中C-H键活化是速率决定步骤。此外，该方法在药物分子合成中的可扩展性和适用性例证了其效用。
