(Fluoromethylsulfonyl)methylation of Quinoxalinones Using NaSO2CH2F for C–F Bond Cleavage

作者：Peng Dai, Yufei Li, Yu Chen, Jian Jiao, Qingqing Wang, Chenxiao Li, Yu‐Cheng Gu, Yanbin Zhang, Qing Xia, Weihua Zhang · 发表于：Organic Letters · 年份：2022 · DOI：10.1021/acs.orglett.2c00048 · 被引用次数：13 · 研究领域：Fluorine in Organic Chemistry、Synthesis and Biological Evaluation、Radical Photochemical Reactions

We developed a facile, efficient, and scalable route to achieve monofluoromethylsulfinyl alkylation of quinoxalinones. NaSO 2 CH 2 F served as the source of methylene to construct new C–C and C–S bonds via C–F bond cleavage. NaSO 2 CH 2 F was also the source of SO 2 CH 2 F. Density functional theory calculations confirmed the proposed mechanism, in which the SO 2 CH 2 F radical is immediately trapped. The reaction exhibited a high level of atom economy. Moreover, some representative products displayed excellent biological activity.