Testing the veracity of claims of Lewis acid catalysis. Issue 50 (12th December 2018)

• Record Type: Journal Article
• Authors: Šolić, Ivan; Lin, Hong Xuan; Bates, Roderick W.
• Is Part Of: Tetrahedron letters. Volume 59:Issue 50(2018)
• Page Start: 4434
• Page End: 4436
• Publication Date: 2018-12-12
• Subjects: Lewis -- Brønsted -- Catalysis -- Hydrolysis -- Hidden; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.11.006
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Brønsted vs. Lewis acid catalysis is tested. For claimed scandium(III), indium(III), iron(III) and yttrium(III) catalysis. Halogen bonding. 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.