Palladium Iodide-Catalyzed Selective Carbonylative Double Cyclization of 4-(2-Aminophenyl)-3-yn-1-ols to Dihydrofuroquinolinone Derivatives

The PdI2/KI-catalyzed oxidative carbonylation of 4-(2-aminophenyl)-3-yn-1-ols, bearing two potential nucleophilic groups in suitable position selectively leads to dihydrofuroquinolinone derivatives in fair to high yields (60%-89%) and excellent turnover numbers (180-267 mol of product per mol of Pd) over 19 examples, through a mechanistic pathway involving initial O-cyclization followed by N-cyclocarbonylation. In such process, the selective catalytic construction of two rings and three new bonds is achieved in one synthetic step to afford high value added fused heterocyclic structures starting from readily available materials.