Synthesis of novel dendritic 2,2'-bipyridine ligands and their application to Lewis acid-catalyzed diels-alder and three-component condensation reactions.

A series of dendritic ligands with a 2,2'-bipyridine core was synthesized through the coupling of 4,4'-dihydroxy-2,2'-bipyridine with poly(aryl ether) dendrons. The corresponding dendritic Cu(OTf)2 catalysts were used for Diels-Alder and three-component condensation reactions. The dendritic Cu(OTf)2-catalyzed Diels-Alder reaction proceeded smoothly, and these dendritic catalysts could be recycled without deactivation by reprecipitation. Three-component condensation reactions such as Mannich-type reactions also proceeded not only in dichloromethane but also in water. Furthermore, a positive dendritic effect on chemical yields was observed in both Diels-Alder reactions and aqueous-media three-component condensation reactions.