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Synthesis, photoinduced amination and topological indices of novel porphyrin dyads
Journal of Porphyrins and Phthalocyanines ( IF 0.9 ) Pub Date : 2020-08-06 , DOI: 10.1142/s1088424620500200
Muhammad Yaseen 1 , Muhammad A. Rashid 2 , Muhammad A. Iqbal 2 , Zahid Farooq 3 , Muhammad Idrees 4 , Muhammad A. Qayyum 1 , Azeem Intisar 5 , Mian HR. Mahmood 1 , Ibrahim Khan 6 , Muhammad Latif 7
Affiliation  

Transition-metal-catalyzed homo and hetero coupling is a rapidly growing area of research. This work refers to the nickel-catalyzed photoinduced amination study of β-bromotetraarylporphyrin and its Ni(II), Zn(II) and Cu(II) complexes. The selective mono β-bromination of 5,10,15,20-tetrakis(4-isopropylphenyl)porphyrin was achieved with N-bromosuccinimide. Under similar conditions, β-bromination of Ni(II), Zn(II) and Cu(II) complexes of 5,10,15,20-tetrakis(4-isopropylphenyl)porphyrin successfully afforded the corresponding 2-bromometalloporphyrins. The β-bromoporphyrin/metalloporphyrins were coupled with three different amines through the creation of the C–N bond by using an economical and air-tolerant photoactive catalyst (NiBr2 · 3H2O) at room temperature under 365 nm radiations. Nickel-catalyzed amination yields are compared with the traditional Buchwald–Hartwig amination yields. Due to the low operational cost, photoinduced nickel-catalyzed C–N couplings were found to be more economical than the Buchwald–Hartwig amination procedure, although the latter afforded higher yields. The nickel-catalyzed photoamination reaction was also extended for the one-pot synthesis of pyridine-3,5-diamine bridged porphyrin dyad. The intramolecular cyclization of the pyridine-3,5-diamine-bridged porphyrin dyad afforded a novel quinolino-fused porphyrin dyad. Degree- and distance-based topological indices of the newly synthesized porphyrins were calculated and correlated with their molar refractivity. All newly synthesized porphyrins are characterized by UV-vis, FTIR, 1H NMR, elemental analysis and mass spectrometry.

中文翻译:

新型卟啉二元体的合成、光诱导胺化和拓扑指标

过渡金属催化的均质和异质偶联是一个快速发展的研究领域。这项工作是指镍催化的光诱导胺化研究β-溴四芳基卟啉及其 Ni(II)、Zn(II) 和 Cu(II) 配合物。选择性单声道β-溴化5,10,15,20-四(4'-异丙基苯基)卟啉是用ñ-溴代琥珀酰亚胺。在类似的条件下,β-溴化 5,10,15,20-四 (4) 的 Ni(II)、Zn(II) 和 Cu(II) 配合物'-异丙基苯基)卟啉成功地提供了相应的2-溴金属卟啉。这β-溴卟啉/金属卟啉通过使用经济且耐空气的光活性催化剂(NiBr2· 3H 2O) 在室温下在 365 nm 辐射下。将镍催化的胺化产率与传统的 Buchwald-Hartwig 胺化产率进行比较。由于操作成本低,发现光诱导镍催化的 C-N 偶联比 Buchwald-Hartwig 胺化过程更经济,尽管后者提供了更高的产率。镍催化的光胺化反应也被扩展到吡啶-3,5-二胺桥联卟啉二联体的一锅法合成。吡啶-3,5-二胺桥联卟啉二联体的分子内环化提供了一种新型的喹啉-稠合卟啉二联体。计算了新合成的卟啉的基于度数和距离的拓扑指数,并与它们的摩尔折射率相关联。所有新合成的卟啉均通过 UV-vis、FTIR、1H NMR,元素分析和质谱。
更新日期:2020-08-06
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