Testing the veracity of claims of Lewis acid catalysis

Ivan Šolić; Hong Xuan Lin; Roderick W. Bates

doi:10.1016/j.tetlet.2018.11.006

Testing the veracity of claims of Lewis acid catalysis

Ivan Šolić, Hong Xuan Lin, Roderick W. Bates^*

^*Corresponding author for this work

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

26 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4434-4436
Number of pages	3
Journal	Tetrahedron Letters
Volume	59
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2018.11.006
Publication status	Published - Dec 12 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2018 Elsevier Ltd

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Brønsted
Catalysis
Hidden
Hydrolysis
Lewis

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10.1016/j.tetlet.2018.11.006

Cite this

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title = "Testing the veracity of claims of Lewis acid catalysis",

abstract = "Are reactions employing Lewis acids really catalysed by those Lewis acids, or by “hidden Br{\o}nsted acids”, i.e. Br{\o}nsted 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 Br{\o}nsted acid catalysed.",

keywords = "Br{\o}nsted, Catalysis, Hidden, Hydrolysis, Lewis",

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year = "2018",

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doi = "10.1016/j.tetlet.2018.11.006",

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T1 - Testing the veracity of claims of Lewis acid catalysis

AU - Šolić, Ivan

AU - Lin, Hong Xuan

AU - Bates, Roderick W.

PY - 2018/12/12

Y1 - 2018/12/12

N2 - 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.

AB - 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.

KW - Brønsted

KW - Catalysis

KW - Hidden

KW - Hydrolysis

KW - Lewis

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Testing the veracity of claims of Lewis acid catalysis

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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