I 2 or I 2 /PIFA one-pot induced system for rapid synthesis of chalcogenated enamides, uracils or 2-pyridones under mild conditions

We have developed a protocol for the β-C(sp 2 )–H chalcogenylation of both endo - and exo -cyclic enamides using stoichiometric amounts of molecular iodine and dichalcogenides at room temperature, completing the reaction within a mere five minutes and in an open-air environment. This method yields a...

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Veröffentlicht in:New journal of chemistry 2024-07, Vol.48 (28), p.12793-12799
Hauptverfasser: Sanaa, Hamdi, Dondasse, Ismaël, Retailleau, Pascal, Nicolas, Cyril, Gillaizeau, Isabelle
Format: Artikel
Sprache:eng
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Zusammenfassung:We have developed a protocol for the β-C(sp 2 )–H chalcogenylation of both endo - and exo -cyclic enamides using stoichiometric amounts of molecular iodine and dichalcogenides at room temperature, completing the reaction within a mere five minutes and in an open-air environment. This method yields a diverse array of sulfenylated and selenated enamide compounds, including 5-phenylsulfanyl and 5-phenylselanyl uracil, under mild and metal-free conditions. Treating the endo -cyclic chalcogenated enamides with PIFA for five minutes, through a sequential one-pot process, leads to valuable 5-thio- and 5-seleno-2-pyridones with a free C-3 position.
ISSN:1144-0546
1369-9261
DOI:10.1039/D4NJ01989J