Abstract
The first metal-free thermal protodeboronation of ortho- and para-phenol boronic acids in DMSO was developed. The protodeboronation was successfully applied to the synthesis of ortho- and meta-functionalized phenols using the boronic acid moiety as a blocking group and a directing group, respectively. Mechanistic studies suggested that this protodeboronation proceeds through the coordination of water to the boron atom followed by σ-bond metathesis.
| Original language | English |
|---|---|
| Pages (from-to) | 12154-12160 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 78 |
| Issue number | 23 |
| DOIs | |
| Publication status | Published - 2013 Dec 6 |
ASJC Scopus subject areas
- Organic Chemistry
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Lee, C. Y., Ahn, S. J., & Cheon, C. H. (2013). Protodeboronation of ortho- and para-phenol boronic acids and application to ortho and meta functionalization of phenols using boronic acids as blocking and directing groups. Journal of Organic Chemistry, 78(23), 12154-12160. https://doi.org/10.1021/jo402174v