A simple and efficient recyclable phosphine-free catalytic system for alkoxycarbonylation and carbonylative Sonogashira coupling reactions of aryl iodides

Abstract

Using palladium on charcoal (Pd/C) and triethylamine as a novel, efficient, versatile, recyclable, and phosphine-free catalytic system, we carried out the alkoxycarbonylation of aryl iodides (alcohols or phenols as nucleophiles) and the carbonylative Sonogashira coupling reaction of aryl iodides with terminal alkynes, affording the corresponding aryl esters and α , β -alkynyl ketones in good to excellent yields under mild conditions. We found that both electron-withdrawing and electron-donating substituents on phenol enhanced the phenoxycarbonylation of iodobenzene. The recyclability of Pd/C was also demonstrated.