Synthesis of hydroxylated azacalix[1]arene[3]pyridines from hydrolysis of high valent arylcopper complexes and conversion to a double azacalix[1]arene[3]pyridine host molecule

文献情報

出版日 2016-11-25

DOI 10.1039/C6QO00669H

インパクトファクター 5.281

著者

Qian Zhang, Mei-Xiang Wang

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要旨

Hydrolysis of shelf-stable and structurally well-defined arylcopper(II) and arylcopper(III) complexes was investigated. Under alkali conditions all arylcopper(II) compounds underwent efficient hydrolysis at ambient temperature to produce exclusively lower-rim-hydroxylated azacalix[1]arene[3]pyridines in excellent yields. The identical products were obtained in only moderate yields from the same hydrolytic reaction of arylcopper(III) compounds. The latter reaction also yielded a 4,4′-biphenol-joint double azacalix[1]arene[3]pyridine product. The double azacalix[1]phenol[3]pyridine was then prepared in good yield from the CuCl2/TMEDA-catalyzed oxidative homocoupling of two azacalix[1]phenol[3]pyridines. The supramolecular application of the resulting double azacalixaromatics was demonstrated by their complexation with aliphatic diamines to form one-dimensional molecular assemblies in the solid state.

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Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Synthesis of hydroxylated azacalix[1]arene[3]pyridines from hydrolysis of high valent arylcopper complexes and conversion to a double azacalix[1]arene[3]pyridine host molecule

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