Testing the veracity of claims of Lewis acid catalysis
Lin, Hong Xuan
Bates, Roderick Wayland
Date of Issue2018
School of Physical and Mathematical Sciences
Are reactions employing Lewis acids really catalysed by those Lewis acids, or by “hidden Brønsted acids”, i.e. Brønsted acids generated in situ by hydrolysis? Testing of a series of reactions using Sc(III), Fe(III), In(III) and Y(III) by addition of 2,6-di-t-butyl-4-methylpyridine reveal that all are likely to follow the latter pathway. A reaction claimed to be catalysed by CBr4 through halogen bonding is also likely to be Brønsted acid catalysed.
© 2018 Elsevier. All rights reserved. This paper was published in Tetrahedron Letters and is made available with permission of Elsevier.