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

Ida Ziccarelli; Lucia Veltri; Tommaso Prestia; Roberta Amuso; Maria A Chiacchio; Raffaella Mancuso; Bartolo Gabriele

doi:10.3390/molecules28196764

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

Molecules. 2023 Sep 22;28(19):6764. doi: 10.3390/molecules28196764.

Authors

Ida Ziccarelli¹, Lucia Veltri¹, Tommaso Prestia¹, Roberta Amuso¹, Maria A Chiacchio², Raffaella Mancuso¹, Bartolo Gabriele¹

Affiliations

¹ Laboratory of Industrial and Synthetic Organic Chemistry (LISOC), Department of Chemistry and Chemical Technologies, University of Calabria, Via Pietro Bucci 12/C, 87036 Arcavacata di Rende, Italy.
² Department of Drug Sciences, University of Catania, Viale A. Doria 6, 95125 Catania, Italy.

Abstract

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.

Keywords: C–H activation; alkynes; amides; aminocarbonylation; carbonylation; conjugate addition; cyclization; furans; oxidative carbonylation; palladium.

Grants and funding

This research received no external funding.