Rational synthesis of benzimidazole[3]arenes by CuII-catalyzed post-macrocyclization transformation†‡,Chemical Science

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Rational synthesis of benzimidazole[3]arenes by CuII-catalyzed post-macrocyclization transformation†‡
Chemical Science ( IF 7.6 ) Pub Date : 2018-09-05 00:00:00 , DOI: 10.1039/c8sc03086c
Shohei Tashiro _{1,

2,

3,

4,

5} , Tsutomu Umeki _{1,

2,

3,

4,

5} , Ryou Kubota _{1,

2,

3,

4,

5} , Mitsuhiko Shionoya _{1,

2,

3,

4,

5}

Affiliation

A new series of calix[n]arene analogues, benzimidazole[3]arenes, was rationally synthesized by Cu^II-catalyzed post-macrocyclization transformation of a tris(o-phenylenediamine) macrocycle, and fully characterized by NMR, MS, and single-crystal X-ray diffraction (XRD) analyses. The resulting syn- and anti-benzimidazole[3]arenes have a bowl-shaped and a warped structure, respectively, in their crystalline states, and both display a dynamic inversion behavior in solution. This modification resulted in strong fluorescence due to the generated benzimidazole moieties. The mechanistic study of the post-macrocyclization transformation demonstrated that the formation of both benzimidazole[3]arenes was catalyzed, via triimine intermediates, by Cu^II ions in air through oxidation and cyclization of the tris(o-phenylenediamine) macrocycle.

中文翻译：

苯并咪唑的合成理性[3]用Cu芳烃^II催化的大环化后变换†往最 ‡

通过Cu ^II催化的三（邻苯二胺）大环的大环环化反应合理合成了一系列新的杯芳烃[ n ]芳烃类似物苯并咪唑[3]芳烃，并通过NMR，MS和单-晶体X射线衍射（XRD）分析。所得的顺式和反式苯并咪唑[3]芳烃在其结晶态下分别具有碗形和翘曲结构，并且在溶液中均显示出动态的反转行为。由于产生的苯并咪唑部分，这种修饰导致强烈的荧光。宏环化后转化的机理研究表明，苯并咪唑[3]芳烃的形成均被催化，通过三亚胺中间体，通过空气中的Cu ^II离子通过三（邻苯二胺）大环的氧化和环化作用。

更新日期：2018-09-05

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