Palladium Iodide Catalyzed Multicomponent Carbonylative Synthesis of 2-(4-Acylfuran-2-yl)acetamides

Autor:	Ida Ziccarelli, Lucia Veltri, Tommaso Prestia, Roberta Amuso, Maria A. Chiacchio, Raffaella Mancuso, Bartolo Gabriele
Jazyk:	angličtina
Rok vydání:	2023
Předmět:	alkynes amides aminocarbonylation carbonylation C–H activation conjugate addition Organic chemistry QD241-441
Zdroj:	Molecules, Vol 28, Iss 19, p 6764 (2023)
Druh dokumentu:	article
ISSN:	1420-3049 40732649
DOI:	10.3390/molecules28196764
Popis:	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.
Databáze:	Directory of Open Access Journals
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