Access to 2‑Alkenyl-furans via a Cascade of Pd-Catalyzed Cyclization / Coupling Followed by Oxidative Aromatization with DDQ

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Authors
Bisek, Bartosz ORCID logo 0000-0003-2020-6068
Chaładaj, Wojciech ORCID logo 0000-0001-8143-3788
Date
2024
Journal Title
Journal ISSN
Volume Title
Publisher
ACS Publications
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Creative Commons License
Attribution 4.0 International
Abstract
An unprecedented DDQ-mediated oxidative aromatization of 2-bezylidene-dihydrofurans yielding 2-alkenyl-furans is disclosed. Integration of this transformation with a prior Pd-catalyzed reaction of α-propargylic-β-ketoesters and (hetero)aryl halides into a one-pot cascade process opens a direct modular route to highly substituted 2-vinyl-furans. Experimental and computational studies reveal that the crucial step of the oxidative-aromatization involves facile hydride transfer from the dihydrofuran ring to the O-center of DDQ.
Description
Citation
J. Org. Chem. 2024, 89, 7275−7279. https://doi.org/10.1021/acs.joc.4c00149
URI
https://open.icm.edu.pl/handle/123456789/24344
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