Palladium-Catalyzed Sequential Alkylation-Alkenylation Reactions and Their Application to the Synthesis of Fused Aromatic Rings

…, JF Paquin, S Piguel, M Dahlmann

Index: Lautens, Mark; Paquin, Jean-Francois; Piguel, Sandrine; Dahlmann, Marc Journal of Organic Chemistry, 2001 , vol. 66, # 24 p. 8127 - 8134

Full Text: HTML

Citation Number: 64

Abstract

The synthesis of fused aromatic carbocycles from aryl iodides and difunctional acceptors is outlined. This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence. Under the optimized conditions (Pd (OAc) 2 (10 mol%), tri-2-furylphosphine (20-30 mol%), norbornene (2 equiv), Cs2CO3 (2 equiv), CH3CN, reflux), bromoenoates react with aryl iodides bearing numerous substituents (F, ...