通过自旋中心转移实现的三氟甲基苯并咪唑的脱氟烷基化反应：一种与一氧化碳协同的光催化/硫醇催化过程
Defluorinative Alkylation of Trifluoromethylbenzimidazoles Enabled by Spin-Center Shift: A Synergistic Photocatalysis/Thiol Catalysis Process with CO
作者信息
Xu Pei, Wang Xing-Yu, Wang Zhijuan, Zhao Jinjin, Cao Xu-Dong, Xiong Xiao-Chun, Yuan Yu-Chao, Zhu Songlei, Guo Dong, Zhu Xu
机构信息
Jiangsu Key Laboratory of New Drug Research and Clinical Pharmacy, School of Pharmacy, Xuzhou Medical University, 209 Tongshan Road, Xuzhou 221004, China.
School of Chemistry and Molecular Engineering (SCME), Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, China.
出版信息
Org Lett. 2022 Jun 10;24(22):4075-4080. doi: 10.1021/acs.orglett.2c01533. Epub 2022 Jun 1.
We describe a catalytic strategy for direct single C(sp)-F bond alkylation of trifluoromethylbenzimidazoles under a photoinduced thiol catalysis process. The CO radical anion (CO) proved to be the most efficient single-electron reductant to realize such a transformation. The spin-center shift of the generated radical anion intermediate is the key step in realizing C-F bond activation under mild conditions with high efficiency.
我们描述了一种在光诱导硫醇催化过程下，用于三氟甲基苯并咪唑直接单C(sp)-F键烷基化的催化策略。事实证明，CO自由基阴离子（CO）是实现这种转化最有效的单电子还原剂。所生成的自由基阴离子中间体的自旋中心转移是在温和条件下高效实现C-F键活化的关键步骤。
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