Functionalisation of Chromane by Deprotonative Metallation
Abstract: Despite the biological interest in chromane derivatives, few studies dedicated to the functionalisation of this heterocycle have been reported. Herein, our objective is to demonstrate the potential of alkali metal bases for the introduction of substituents at its positions 4 and 8, and to explain the observed reactivity based on quantum chemical calculations. Guided by these theoretical results, preliminary optimisation was carried out on 2,3‐dihydrobenzofuran before applying the optimal conditions to chromane. Deprotolithiation at C8 was thus achieved using n‐butyllithium in hexane at room temperature, while functionalisation at C4 was promoted by a 1:1 mixture of lithium 2,2,6,6‐tetramethylpiperidide and potassium tert‐butoxide in tetrahydrofuran at −50 °C. Various electrophiles were used to intercept the lithiated intermediates, providing a convenient access to substituted chromane derivatives.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Functionalisation of Chromane by Deprotonative Metallation ; day:15 ; month:08 ; year:2024 ; extent:9
European journal of organic chemistry ; (15.08.2024) (gesamt 9)
- Creator
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Bastien, Cléo
Erb, William
Halauko, Yury S.
Matulis, Vadim E.
Roisnel, Thierry
Sarazin, Yann
Mongin, Florence
- DOI
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10.1002/ejoc.202400566
- URN
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urn:nbn:de:101:1-2408161410064.574096335451
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:52 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Bastien, Cléo
- Erb, William
- Halauko, Yury S.
- Matulis, Vadim E.
- Roisnel, Thierry
- Sarazin, Yann
- Mongin, Florence
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