Abstract
A combination of pentafluorophenylboronic acid and oxalic acid catalyses the dehydrative substitution of benzylic alcohols with a second alcohol to form new C‐O bonds. This method has been applied to the intermolecular substitution of benzylic alcohols to form symmetrical ethers, intramolecular cyclisations of diols to form aryl‐substituted tetrahydrofuran and tetrahydropyran derivatives, and intermolecular crossed‐etherification reactions between two different alcohols. Mechanistic control experiments have identified a potential catalytic intermediate formed between the arylboronic acid and oxalic acid.
| Original language | English |
|---|---|
| Pages (from-to) | 3950-3956 |
| Number of pages | 7 |
| Journal | Chemistry - A European Journal |
| Volume | 25 |
| Issue number | 15 |
| Early online date | 10 Jan 2019 |
| DOIs | |
| Publication status | Published - 12 Mar 2019 |
Keywords
- alcohols
- boronic acids
- etherification
- homogeneous catalysis
- substitution
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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Data for Aryl boronic acid-catalysed dehydrative substitution of benzylic alcohols for C-O bond formation
Estopina-Duran, S. (Creator), Donnelly, L. (Creator), Mclean, E. (Creator), Hockin, B. (Creator), Slawin, A. M. Z. (Creator) & Taylor, J. (Creator), University of Bath, 10 Jan 2019
DOI: 10.15125/BATH-00561
Dataset