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Lithiation‐functionalisation of triazoles bearing electron‐withdrawing N‐substituents : challenges and solutions
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Bugden, Frances E., Clarkson, Guy J. and Greenhalgh, Mark David (2023) Lithiation‐functionalisation of triazoles bearing electron‐withdrawing N‐substituents : challenges and solutions. European Journal of Organic Chemistry, 26 (5). e202201459. doi:10.1002/ejoc.202201459 ISSN 1434-193X.
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Official URL: https://doi.org/10.1002/ejoc.202201459
Abstract
The regioselective lithiation of 1,2,3-triazoles provides an opportunity to introduce additional functionality, however this simple functionalisation strategy using triazoles bearing electron-withdrawing N-substituents has not been investigated until now. Herein, we demonstrate that the lithiated triazole intermediates can readily decompose, even at −78 °C. In addition, lithiation-deuteration studies reveal lithiation can take place competitively on both the triazole and the electron-withdrawn aryl ring. Careful control of reaction conditions is therefore required to i) minimise decomposition pathways; and ii) facilitate regioselective functionalisation of the triazole.
Item Type: | Journal Article | ||||||||
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Subjects: | Q Science > QD Chemistry | ||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||
SWORD Depositor: | Library Publications Router | ||||||||
Library of Congress Subject Headings (LCSH): | Triazoles , Electrons | ||||||||
Journal or Publication Title: | European Journal of Organic Chemistry | ||||||||
Publisher: | Wiley ; V.C.H Verlag | ||||||||
ISSN: | 1434-193X | ||||||||
Official Date: | 1 February 2023 | ||||||||
Dates: |
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Volume: | 26 | ||||||||
Number: | 5 | ||||||||
Article Number: | e202201459 | ||||||||
DOI: | 10.1002/ejoc.202201459 | ||||||||
Status: | Peer Reviewed | ||||||||
Publication Status: | Published | ||||||||
Re-use Statement: | This is the peer reviewed version of the following article: Bugden, F.E., Clarkson, G.J. and Greenhalgh, M.D. (2023), Lithiation-Functionalisation of Triazoles Bearing Electron-Withdrawing N-Substituents: Challenges and Solutions. Eur. J. Org. Chem. , which has been published in final form at https://doi.org/10.1002/ejoc.202201459. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited. | ||||||||
Access rights to Published version: | Open Access (Creative Commons) | ||||||||
Date of first compliant deposit: | 5 January 2023 | ||||||||
Date of first compliant Open Access: | 16 December 2023 | ||||||||
RIOXX Funder/Project Grant: |
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