Academic Journal
Palladium Iodide Catalyzed Multicomponent Carbonylative Synthesis of 2-(4-Acylfuran-2-yl)acetamides
| Title: | Palladium Iodide Catalyzed Multicomponent Carbonylative Synthesis of 2-(4-Acylfuran-2-yl)acetamides |
|---|---|
| Authors: | Ida Ziccarelli, Lucia Veltri, Tommaso Prestia, Roberta Amuso, Maria A. Chiacchio, Raffaella Mancuso, Bartolo Gabriele |
| Source: | Molecules, Vol 28, Iss 19, p 6764 (2023) |
| Publisher Information: | MDPI AG, 2023. |
| Publication Year: | 2023 |
| Collection: | LCC:Organic chemistry |
| Subject Terms: | alkynes, amides, aminocarbonylation, carbonylation, C–H activation, conjugate addition, Organic chemistry, QD241-441 |
| More Details: | 2-Propargyl-1,3-dicarbonyl compounds have been carbonylated under oxidative conditions and with the catalysis of the PdI2/KI catalytic system to selectively afford previously unreported 2-(4-acylfuran-2-yl)acetamides in fair to good yields (54–81%) over 19 examples. The process takes place under relatively mild conditions and occurs via a mechanistic pathway involving Csp-H activation by oxidative monoamincarbonylation of the terminal triple bond of the substrates with formation of 2-ynamide intermediates, followed by 5-exo-dig O-cyclization (via intramolecular conjugate addition of the in situ formed enolate to the 2-ynamide moiety) and aromative isomerization. |
| Document Type: | article |
| File Description: | electronic resource |
| Language: | English |
| ISSN: | 1420-3049 40732649 |
| Relation: | https://www.mdpi.com/1420-3049/28/19/6764; https://doaj.org/toc/1420-3049 |
| DOI: | 10.3390/molecules28196764 |
| Access URL: | https://doaj.org/article/28d55e40732649f6b77a1671eb3fdfb6 |
| Accession Number: | edsdoj.28d55e40732649f6b77a1671eb3fdfb6 |
| Database: | Directory of Open Access Journals |
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