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Testing the veracity of claims of Lewis acid catalysis
Authors:Ivan Šolić  Hong Xuan Lin  Roderick W. Bates
Affiliation:Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore
Abstract: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.
Keywords:Lewis  Brønsted  Catalysis  Hydrolysis  Hidden
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