Citation: Jiaqi Jia, Kathiravan Murugesan, Chen Zhu, Huifeng Yue, Shao-Chi Lee, Magnus Rueping. Multiphoton photoredox catalysis enables selective hydrodefluorinations[J]. Chinese Chemical Letters, ;2025, 36(2): 109866. doi: 10.1016/j.cclet.2024.109866 shu

Multiphoton photoredox catalysis enables selective hydrodefluorinations

KAUST Catalysis Center, KCC, King Abdullah University of Science and Technology, KAUST, Thuwal 23955-6900, Saudi Arabia

magnus.rueping@kaust.edu.sa

Received Date: 20 January 2024
Revised Date: 27 March 2024
Accepted Date: 7 April 2024
Available Online: 8 April 2024

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Late-stage modification of complex molecules via site-selective hydrodefluorination is a challenging endeavor. The selective activation of carbon-fluorine (C–F) bonds in the presence of multiple C–F bonds is of importance in organic synthesis and drug discovery. Herein, we describe the activation of C-F bonds via multiphoton photoredox catalysis to selectively produces a series of hydrodefluorinated compounds by simply tuning the reaction conditions. Moreover, this protocol was successfully applied to the late-stage functionalization of different drug-derivatives and the corresponding mono-, di-, and tri-defluorinated products were obtained in good to excellent yields. A detailed mechanistic investigation provides insight into the unprecedented hydrodefluorination pathway.
- Photoredox catalysis,
- C-F bond activation,
- Site-selectivity,
- Multiphoton,
- Trifluoroacetamide
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