Synthesis of novel dendritic 2,2'-bipyridine ligands and their application to Lewis acid-catalyzed diels-alder and three-component condensation reactions.
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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DOI：
10.1021/jo070767a
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发表时间：
2007-09
期刊：
影响因子：
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通讯作者：
T. Muraki;Ken-Ichi Fujita;Masato Kujime
中科院分区：
文献类型：
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作者：
T. Muraki;Ken-Ichi Fujita;Masato Kujime
通过4，4 ′-二羟基-2，2 ′-联吡啶与聚芳醚树枝状分子的偶联反应，合成了一系列以2，2 ′-联吡啶为核的树枝状配体。相应的树枝状Cu（OTf）2催化剂用于Diels-Alder和三组分缩合反应。树枝状Cu（OTf）2催化的Diels-Alder反应进行顺利，这些树枝状催化剂可以重复使用而不会因再沉淀而失活。三组分缩合反应，如曼尼希型反应不仅在二氯甲烷中，而且在水中也进行。此外，在Diels-Alder反应和水介质三组分缩合反应中都观察到了对化学产率的正树枝化效应。
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.