Synthesis of novel dendritic 2,2'-bipyridine ligands and their application to Lewis acid-catalyzed diels-alder and three-component condensation reactions |
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Authors: | Muraki Takahito Fujita Ken-ichi Kujime Masato |
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Institution: | National Institute of Advanced Industrial Science and Technology (AIST), AIST Tsukuba Central 5, 1-1-1, Higashi, Tsukuba, Ibaraki 305-8565, Japan. |
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Abstract: | 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. |
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