Testing the veracity of claims of Lewis acid catalysis
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 ar...
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sg-ntu-dr.10356-832692023-02-28T19:32:32Z Testing the veracity of claims of Lewis acid catalysis Šolić, Ivan Lin, Hong Xuan Bates, Roderick Wayland School of Physical and Mathematical Sciences Brønsted Lewis Science::Chemistry::Organic chemistry 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. ASTAR (Agency for Sci., Tech. and Research, S’pore) Accepted version 2019-10-03T07:56:07Z 2019-12-06T15:18:51Z 2019-10-03T07:56:07Z 2019-12-06T15:18:51Z 2018 Journal Article Šolić, I., Lin, H. X., & Bates, R. W. (2018). Testing the veracity of claims of Lewis acid catalysis. Tetrahedron Letters, 59(50), 4434-4436. doi:10.1016/j.tetlet.2018.11.006 0040-4039 https://hdl.handle.net/10356/83269 http://hdl.handle.net/10220/50080 10.1016/j.tetlet.2018.11.006 en Tetrahedron Letters © 2018 Elsevier. All rights reserved. This paper was published in Tetrahedron Letters and is made available with permission of Elsevier. 3 p. application/pdf |
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Brønsted Lewis Science::Chemistry::Organic chemistry |
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Brønsted Lewis Science::Chemistry::Organic chemistry Šolić, Ivan Lin, Hong Xuan Bates, Roderick Wayland Testing the veracity of claims of Lewis acid catalysis |
| description |
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. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Šolić, Ivan Lin, Hong Xuan Bates, Roderick Wayland |
| format |
Article |
| author |
Šolić, Ivan Lin, Hong Xuan Bates, Roderick Wayland |
| author_sort |
Šolić, Ivan |
| title |
Testing the veracity of claims of Lewis acid catalysis |
| title_short |
Testing the veracity of claims of Lewis acid catalysis |
| title_full |
Testing the veracity of claims of Lewis acid catalysis |
| title_fullStr |
Testing the veracity of claims of Lewis acid catalysis |
| title_full_unstemmed |
Testing the veracity of claims of Lewis acid catalysis |
| title_sort |
testing the veracity of claims of lewis acid catalysis |
| publishDate |
2019 |
| url |
https://hdl.handle.net/10356/83269 http://hdl.handle.net/10220/50080 |
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1759854952761524224 |