Synthesis of [3]Rotaxanes by the Combination of Copper-Mediated Coupling Reaction and Metal-Template Approach

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• 作者：Ryuto Hayashi ; Yuichiro Mutoh ; Takeshi Kasama ; Shinichi Saito
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：August 7, 2015
• 年：2015
• 卷：80
• 期：15
• 页码：7536-7546
• 全文大小：712K
• ISSN：1520-6904

文摘

[3]Rotaxanes with two axle components and one ring component were synthesized by the combination of a coupling reaction using a transition-metal catalyst and a metal-template approach. Thus, [2]rotaxanes were prepared by the oxidative dimerization of alkyne promoted by macrocyclic phenanthroline鈥揅uI complexes. The [2]rotaxane was reacted with a Cu^I salt and an acyclic ligand to generate a tetrahedral Cu^I complex. Metal-free [3]rotaxane was isolated by the end-capping reaction of the acyclic ligand, followed by the removal of Cu^I ion. The stability of the tetrahedral Cu^I complexes depended on the size of both the ring component and the acyclic ligand, which was correlated with the yield of the corresponding [3]rotaxane.