官能化杂环连接的卟啉：催化作用至关重要。
Functionalized heterocycle-appended porphyrins: catalysis matters.
作者信息
Abdulaeva Inna A, Birin Kirill P, Polivanovskaia Daria A, Gorbunova Yulia G, Tsivadze Aslan Yu
机构信息
A.N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS Leninsky pr., 31, building 4 Moscow 119071 Russia
N.S. Kurnakov Institute of General and Inorganic Chemistry RAS Leninsky pr., 31 Moscow 119991 Russia.
出版信息
RSC Adv. 2020 Nov 23;10(69):42388-42399. doi: 10.1039/d0ra08603g. eCollection 2020 Nov 17.
The scope and limitations of the condensation of labile 2,3-diaminoporphyrin derivatives with aromatic aldehydes to provide functionalized imidazole- and pyrazine-appended porphyrins were investigated in detail. The presence of an acidic catalyst in the reaction was found to be a tool that allows the reaction path to be switched. The influence of the electronic origin of the substituents in the carbonyl components of the condensation on the yields and selectivity of the reaction was revealed. Metal-promoted cross-coupling transformations were found to be convenient for the further targeted construction of functional derivatives based on the prepared bromo-substituted pyrazinoporphyrins. Overall, these strategies provide a versatile technique for the elaboration of a variety of functionalized heterocycle-appended porphyrins for further application in the development of hybrid materials.
详细研究了不稳定的2,3-二氨基卟啉衍生物与芳香醛缩合以提供官能化的咪唑和吡嗪附加卟啉的范围和局限性。发现反应中酸性催化剂的存在是一种能够切换反应路径的工具。揭示了缩合反应中羰基组分中取代基的电子来源对反应产率和选择性的影响。发现金属促进的交叉偶联转化便于基于制备的溴代吡嗪卟啉进一步有针对性地构建功能衍生物。总体而言，这些策略为制备各种官能化杂环附加卟啉提供了一种通用技术，可进一步应用于杂化材料的开发。
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