Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C−O Bond Formation |
| |
| Authors: | Susana Estopiñá-Durán Liam J Donnelly Euan B Mclean Bryony M Hockin Prof Alexandra M Z Slawin Dr James E Taylor |
| |
| Institution: | EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST UK |
| |
| 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 aryl boronic acid and oxalic acid. |
| |
| Keywords: | alcohols boronic acids etherification homogeneous catalysis substitution |
|
|
