Defluorinative Alkylation of Trifluoromethylbenzimidazoles Enabled by Spin-Center Shift: A Synergistic Photocatalysis/Thiol Catalysis Process with CO<sub>2</sub><sup>•–</sup>
Pei Xu, Xingyu Wang, Zhijuan Wang, Jinjin Zhao, Xudong Cao, Xiaochun Xiong, Yu‐Chao Yuan, Songlei Zhu, Dong Guo, Xu Zhu
Abstract
We describe a catalytic strategy for direct single C(sp3)–F bond alkylation of trifluoromethylbenzimidazoles under a photoinduced thiol catalysis process. The CO2 radical anion (CO2•–) 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.
Topics & Concepts
ChemistryPhotocatalysisAlkylationCatalysisThiolPhotochemistryIonRadical ionCatalytic cycleSpin (aerodynamics)Combinatorial chemistryOrganic chemistryAerospace engineeringEngineeringFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques