Access to 2‑Alkenyl-furans via a Cascade of Pd-Catalyzed Cyclization / Coupling Followed by Oxidative Aromatization with DDQ
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| dc.contributor.author | Bisek, Bartosz | |
|---|---|---|
| dc.contributor.author | Chaładaj, Wojciech | |
| dc.contributor.organization | Institute of Organic Chemistry, Polish Academy of Sciences | |
| dc.date.accessioned | 2024-06-03T13:24:36Z | |
| dc.date.available | 2024-06-03T13:24:36Z | |
| dc.date.issued | 2024 | |
| dc.description.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. | en |
| dc.description.sponsorship | Polish National Science Centre (Grant 2016/22/E/ST5/00537); Wroclaw Centre for Networking and Supercomputing, grant no. 518 | |
| dc.identifier.citation | J. Org. Chem. 2024, 89, 7275−7279. https://doi.org/10.1021/acs.joc.4c00149 | |
| dc.identifier.doi | 10.1021/acs.joc.4c00149 | |
| dc.identifier.issn | 0022-3263 | |
| dc.identifier.issn | 1520-6904 | |
| dc.identifier.uri | https://open.icm.edu.pl/handle/123456789/24344 | |
| dc.language.iso | en | |
| dc.publisher | ACS Publications | |
| dc.rights | Uznanie autorstwa 4.0 Międzynarodowe | en |
| dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | |
| dc.source | The Journal of Organic Chemistry | |
| dc.title | Access to 2‑Alkenyl-furans via a Cascade of Pd-Catalyzed Cyclization / Coupling Followed by Oxidative Aromatization with DDQ | en |
| dc.type | article | |
| dc.type.version | publishedVersion | |
| person.identifier.orcid | Bisek, Bartosz [0000-0003-2020-6068] | |
| person.identifier.orcid | Chaładaj, Wojciech [0000-0001-8143-3788] |
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