Premium
Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C−O Bond Formation
Author(s) -
EstopiñáDurán Susana,
Donnelly Liam J.,
Mclean Euan B.,
Hockin Bryony M.,
Slawin Alexandra M. Z.,
Taylor James E.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201806057
Subject(s) - chemistry , aryl , oxalic acid , intramolecular force , boronic acid , tetrahydrofuran , medicinal chemistry , catalysis , intermolecular force , alcohol , organic chemistry , molecule , solvent , alkyl
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.