Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation

Abstract

In this research, ethyl levulinate, methyl levulinate, and 2-methyltetrahydrofuran as bio-derived hemicellulose-based solvents were applied as green alternatives in palladium-catalyzed aminocarbonylation reactions. Iodobenzene and morpholine were used in optimization reactions under different conditions, such as temperatures, pressures, and ligands. It was shown that the XantPhos ligand had a great influence on conversion (98%) and chemoselectivity (100% carboxamide), compared with the monodentate PPh3. Following this study, the optimized conditions were used to extend the scope of substrates with nineteen candidates (various para-, ortho-, and meta-substituted iodobenzene derivatives and iodo-heteroarenes), as well as eight different amine nucleophiles.

Decarbonylation of benzaldehydes by dual photoorgano-cobalt catalysis

“…Furthermore, carbon monoxide evolution was confirmed by gas chromatography (Fig. S17, ESI †) and by performing an aminocarbonylation test reaction, 18 wherein the anxiolytic drug moclobemide 19 could be obtained in good yield (Scheme 5). Under air 16…”

Recent Advances in Catalytic Carbonylation Reactions in Alternative Reaction Media

“…Moreover, good to excellent conversion (32%—100%) was achieved with various iodobenzene derivatives and amines under the optimal reaction conditions (50 °C, 1 bar CO)(Scheme 54). [ 156 ]…”