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001-es BibID:	BIBFORM118376
035-os BibID:	(WoS)001146487300001 (Scopus)85182560676
Első szerző:	Chniti, Sami
Cím:	Synthesis of Chroman-2,4-diones via Ring-Opening/Ring-Closing Reaction Involving Palladium-Catalyzed Intramolecular Aryloxycarbonylation / Sami Chniti, Péter Pongrácz,László Kollár, Attila Bényei,Ágnes Dörnyei, Attila Takács
Dátum:	2024
ISSN:	0022-3263 1520-6904
Megjegyzések:	Palladium-catalyzed aminocarbonylation of 3-iodochromone was studied in the presence of primary and secondary amines using atmospheric pressure of carbon monoxide as a carbonyl source. This procedure successfully provided a library of chromone-3-carboxamides and 3-substituted chroman-2,4-diones in 40 to 92% isolated yields. The reaction proceeded via highly chemoselective aminocarbonylation (up to 100%) in the presence of secondary amines by using monodentate or bidentate phosphine ligands. The tendency of 3-iodochromone substrate to undergo ANRORC rearrangement with N-nucleophiles was crucial to shift the reaction toward an unprecedented chemoselective carbonylative transformation, where a late-stage carbonyl insertion is favored concomitantly to the last ring-closure step. The proposed azaMichael addition/ring-opening/intramolecular aryloxycarbonylation sequence showed compatibility, uniquely, to primary amines when XantPhos was used as a ligand. The solid-state structures of chromone-3-carboxamide (2a) and chroman-2,4-dione (3s) were undoubtedly established by single-crystal XRD analysis. A catalytic cycle was proposed to rationalize the formation of the two types of carbonylated compounds.
Tárgyszavak:	Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban folyóiratcikk katalízis palladium alkoxikarbonlieyzés ROMP
Megjelenés:	Journal of Organic Chemistry. - 89 : 2 (2024), p. 1175-1183. -
További szerzők:	Pongrácz Péter Kollár László Bényei Attila (1962-) (vegyész) Dörnyei Ágnes Takács Attila
Pályázati támogatás:	GINOP-2.3.3-15-2016-00004 GINOP TKP2021-EGA-17 Egyéb
Internet cím:	Szerző által megadott URL DOI Intézményi repozitóriumban (DEA) tárolt változat
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