Construction of Highly Functionalized 2‑Styrylfurans by N‑Heterocyclic Carbene/Brønsted Acid Catalysis

This research presents an original method for synthesizing styrylfurans using N-heterocyclic carbenes (NHCs) and Brønsted acid catalysis. By exploiting 2,4-dioxoesters as conjugated 1,3-dicarbonyls, we have developed a technique allowing the efficient formation of highly functionalized styrylfurans...

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Bibliographic Details
Published in:Organic letters 2024-05, Vol.26 (17), p.3514-3518
Main Authors: Barańska, Izabela, Ośmiałowski, Borys, Rafińska, Katarzyna, Rafiński, Zbigniew
Format: Article
Language:English
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Letter
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Summary:This research presents an original method for synthesizing styrylfurans using N-heterocyclic carbenes (NHCs) and Brønsted acid catalysis. By exploiting 2,4-dioxoesters as conjugated 1,3-dicarbonyls, we have developed a technique allowing the efficient formation of highly functionalized styrylfurans with interesting photochemical properties, through a NHC-catalyzed cross-benzoin reaction followed by a Brønsted acid-driven Paal-Knorr-like condensation. This approach permits the integration of various substituents on the furan ring, with preliminary biological studies indicating potential as fluorescent dyes.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00836