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Catalytic SNAr Hydroxylation and Alkoxylation of Aryl Fluorides.
- Source :
-
Angewandte Chemie . 9/6/2021, Vol. 133 Issue 37, p20554-20562. 9p. - Publication Year :
- 2021
-
Abstract
- Nucleophilic aromatic substitution (SNAr) is a powerful strategy for incorporating a heteroatom into an aromatic ring by displacement of a leaving group with a nucleophile, but this method is limited to electron‐deficient arenes. We have now established a reliable method for accessing phenols and phenyl alkyl ethers via catalytic SNAr reactions. The method is applicable to a broad array of electron‐rich and neutral aryl fluorides, which are inert under classical SNAr conditions. Although the mechanism of SNAr reactions involving metal arene complexes is hypothesized to involve a stepwise pathway (addition followed by elimination), experimental data that support this hypothesis is still under exploration. Mechanistic studies and DFT calculations suggest either a stepwise or stepwise‐like energy profile. Notably, we isolated a rhodium η5‐cyclohexadienyl complex intermediate with an sp3‐hybridized carbon bearing both a nucleophile and a leaving group. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ALKOXYLATION
*ALKYL ethers
*PHENYL ethers
*HYDROXYLATION
*CLASSICAL conditioning
Subjects
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 133
- Issue :
- 37
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 152166393
- Full Text :
- https://doi.org/10.1002/ange.202106440