Abstract
A general and efficient strategy to synthesize 1,2-ambiphilic aromatic and heteroaromatic synthons from haloarenes has been developed. The method involves installation of the PyDipSi directing group, and subsequent palladium-catalyzed directed ortho-halogenation of aryl silanes (see scheme; Py=2-pyridyl). The usefulness of these 1,2-ambiphilic building blocks was shown in their participation as both nucleophilic aryl silane and electrophilic aryl iodide moieties.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 8729-8732 |
| Number of pages | 4 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 49 |
| Issue number | 46 |
| DOIs | |
| State | Published - Nov 8 2010 |
Keywords
- C-H activation
- benzynes
- halogenation
- palladium
- siloles
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
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Dudnik, A. S., Chernyak, N., Huang, C., & Gevorgyan, V. (2010). A general strategy toward aromatic 1,2-ambiphilic synthons: Palladium-catalyzed ortho-halogenation of PyDipSi-arenes. Angewandte Chemie - International Edition, 49(46), 8729-8732. https://doi.org/10.1002/anie.201004426