Abstract
We describe a metal-free, photocatalytic hydrodefluorination (HDF) of polyfluoroarenes (FA) using pyrene-based photocatalysts (Py). The weak “π-hole−π” interaction between Py and FA promotes the electron transfer against unfavorable energetics (ΔGET up to 0.63 eV) and initiates the subsequent HDF. The steric hindrance of Py and FA largely dictates the HDF reaction rate, pointing to an inner-sphere electron transfer pathway. This work highlights the importance of the size and shape of the photocatalyst and the substrate in controlling the electron transfer mechanism and rates as well as the overall photocatalytic processes.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 15805-15808 |
| Number of pages | 4 |
| Journal | Journal of the American Chemical Society |
| Volume | 138 |
| Issue number | 49 |
| DOIs | |
| State | Published - Dec 14 2016 |
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
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Cite this
Lu, J., Khetrapal, N. S., Johnson, J. A., Zeng, X. C., & Zhang, J. (2016). “π-Hole−π” Interaction Promoted Photocatalytic Hydrodefluorination via Inner-Sphere Electron Transfer. Journal of the American Chemical Society, 138(49), 15805-15808. https://doi.org/10.1021/jacs.6b08620