CINECA IRIS Institutional Research Information System
IRIS è la soluzione IT che facilita la raccolta e la gestione dei dati relativi alle attività e ai prodotti della ricerca. Fornisce a ricercatori, amministratori e valutatori gli strumenti per monitorare i risultati della ricerca, aumentarne la visibilità e allocare in modo efficace le risorse disponibili.
EnglishA mild, general, and convenient palladium-catalyzed direct arylation of the 5-position of azoles with aryl bromides, efficiently promoted by tetrabutylammonium acetate, is described. 1-Methylpyrazole, oxazole, and thiazole reacted at 70 degrees C in N,N-dimethylacetamide by using Pd(OAc)(2) as the catalyst precursor. Electron-poor and -rich functional groups, including the free hydroxy group, are well tolerated in the electrophilic partner. A variety of 5-aryl-1-methylimidazoles were also very efficiently obtained simply by raising the reaction temperature to 110 degrees C. This ligand-free protocol was successfully applied to the one-pot synthesis of two bioactive natural compounds, balsoxin and texaline, starting from oxazole by sequential direct arylation of the 5- and 2-positions.
| Autori interni: | ||
| Autori: | Bellina, Fabio; Lessi, Marco; Manzini, Chiara | |
| Titolo: | Mild Palladium-Catalyzed Regioselective Direct Arylation of Azoles Promoted by Tetrabutylammonium Acetate | |
| Anno del prodotto: | 2013 | |
| Abstract: | A mild, general, and convenient palladium-catalyzed direct arylation of the 5-position of azoles with aryl bromides, efficiently promoted by tetrabutylammonium acetate, is described. 1-Methylpyrazole, oxazole, and thiazole reacted at 70 degrees C in N,N-dimethylacetamide by using Pd(OAc)(2) as the catalyst precursor. Electron-poor and -rich functional groups, including the free hydroxy group, are well tolerated in the electrophilic partner. A variety of 5-aryl-1-methylimidazoles were also very efficiently obtained simply by raising the reaction temperature to 110 degrees C. This ligand-free protocol was successfully applied to the one-pot synthesis of two bioactive natural compounds, balsoxin and texaline, starting from oxazole by sequential direct arylation of the 5- and 2-positions. | |
| Digital Object Identifier (DOI): | 10.1002/ejoc.201300704 | |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
File in questo prodotto:
Copyright © 2022