Journal article
Palladium-Catalyzed Cross-Coupling Reactions with Fluorinated Substrates: Mechanistic Insights into the Undesired Hydrodehalogenation of Aryl Halides
Organometallics, Vol.31(4), pp.1271-1274
Feb/2012
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.
Details
- Title
- Palladium-Catalyzed Cross-Coupling Reactions with Fluorinated Substrates; Mechanistic Insights into the Undesired Hydrodehalogenation of Aryl Halides
- Creators
- Meital Orbach (null) - The Weizmann Institute of ScienceJoyanta Choudhury (null) - The Weizmann Institute of ScienceMichal Lahav (null) - The Weizmann Institute of ScienceOlena V. Zenkina (null)Yael Diskin Posner (null) - 972WIS_INST___100Gregory Leitus (null) - 972WIS_INST___100Mark A. Iron (null)Milko E. van der Boom (null) - The Weizmann Institute of Science
- Resource Type
- Journal article
- Publication Details
- Organometallics, Vol.31(4), pp.1271-1274; Feb/2012
- Number of pages
- 4
- Language
- English
- DOI
- https://doi.org/10.1021/om200898t
- Grant note
- This research was supported by the Helen and Martin Kimmel Center for Molecular Design. J.C. thanks the EU (FP7 program) for an Incoming Marie Curie fellowship. Dr. A. C. B. Lucassen is acknowledged for his assistance. M.E.v.d.B. is the incumbent of the Bruce A. Pearlman Professorial Chair in Synthetic Organic Chemistry._ALMAME_DELIMITER_
- Record Identifier
- 993264519603596
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