Abstract
We report here that the undesired hydrodehalogenation in cross-coupling reactions with fluorinated substrates involves water as a possible hydrogen source. Moreover, the product distribution (hydrodehalogenation vs carbon-carbon coupling) can be controlled by varying the phosphine substituents. Significant hydrodehalogenation occurs prior to the formation of Ar F-Pd(II)-Br complexes. DFT calculations were used to evaluate a direct hydrodehalogenation route with a phosphine and water. These findings provide new mechanistic insight into aryl-Br bond activation with fluorinated substrates and selective arene functionalization.
| Original language | English |
|---|---|
| Pages (from-to) | 1271-1274 |
| Number of pages | 4 |
| Journal | Organometallics |
| Volume | 31 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - Feb 27 2012 |
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
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Orbach, M., Choudhury, J., Lahav, M., Zenkina, O. V., Diskin-Posner, Y., Leitus, G., Iron, M. A., & Van Der Boom, M. E. (2012). Palladium-catalyzed cross-coupling reactions with fluorinated substrates: Mechanistic insights into the undesired hydrodehalogenation of aryl halides. Organometallics, 31(4), 1271-1274. https://doi.org/10.1021/om200898t