Journal of Porphyrins and Phthalocyanines ( IF 0.9 ) Pub Date : 2021-05-07 , DOI: 10.1142/s1088424621500504 Valentinos Mouarrawis 1 , Simon Mathew 1 , Eva J. Meeus 1 , Bas de Bruin 1 , Joost Reek 1
A facile synthetic strategy was developed for the synthesis of meso -tetrakis(4-formyl-phenyl)porphyrin and meso -tetrakis(3-formylphenyl)porphyrin from commercially available starting materials. This method gives facile access to practical amounts of these synthons in high purity and good overall yield, without employing laborious chromatographic separations. The reduction of the respective carboxylic acid-functionalized porphyrins by LiAlH4 afforded the tetra(benzylalcohol)porphyrin intermediates, subsequently utilized in a Parikh-Doering oxidation to selectively afford the desired tetraformylated products. The inherent ease of synthesis of these porphyrin building blocks provides a convenient pathway for the synthesis of various macromolecular and supramolecular architectures for applied chemical technologies.
中文翻译:
内消旋四(4-甲酰基苯基)卟啉和内消旋四(3-甲酰基苯基)卟啉的无色谱合成:超分子和大分子化学中的多功能合成子
开发了一种简便的合成策略,用于从市售起始材料合成内消旋四(4-甲酰基苯基)卟啉和内消旋四(3-甲酰基苯基)卟啉。这种方法可以很容易地以高纯度和良好的总收率获得实际数量的这些合成子,而无需使用费力的色谱分离。LiAlH 4还原相应的羧酸功能化卟啉提供了四(苄醇)卟啉中间体,随后用于 Parikh-Doering 氧化以选择性地提供所需的四甲酰化产物。这些卟啉结构单元固有的合成简单性为应用化学技术合成各种大分子和超分子结构提供了便利的途径。