Synthesis of fluorinated acid-functionalized, electron-rich nickel porphyrins

• Mike Brockmann,
• Jonas Lobbel,
• Lara Unterriker and
• Rainer Herges

Beilstein J. Org. Chem. 2024, 20, 2954–2958, doi:10.3762/bjoc.20.248

• ; perfluorinated aliphatic carboxylic acids; porphyrin synthesis; Introduction Metal porphyrins are prosthetic groups in a number of essential biomolecules, including hemoglobin, chlorophyll, and cytochromes, supporting processes such as oxygen transport, photosynthesis, and electron transfer [1][2][3][4][5

• ether reactions with 2-hydroxy-3,4,5-trimethoxybenzaldehyde (21) to prepare the aldehyde component for a Rothemund-type porphyrin synthesis of acid-functionalized electron-rich porphyrins. The corresponding Ni porphyrins are potential compounds for electrocatalysis and sensor applications. The ω

• ester-functionalized aldehydes 22, 23, and 24. Conditions: a) NIS, TFA, Na2CO3, MeCN, reflux, 18 h; b) Cu2O·H2O, 2-pyridinaldoxime, TBAB, CsOH, H2O, N2, rt, 18 h; c) Cs2CO3, DMAc, N2, rt, 3 h. Porphyrin synthesis. a) Rothemund porphyrin synthesis of metal-free porphyrins 26, 27, and 28; b) metalation of

Substituent-controlled construction of A₄B₂-hexaphyrins and A₃B-porphyrins: a mechanistic evaluation

• Seda Cinar,
• Dilek Isik Tasgin and
• Canan Unaleroglu

Beilstein J. Org. Chem. 2023, 19, 1832–1840, doi:10.3762/bjoc.19.135

• screened in the literature. To the best of our knowledge, hexaphyrin synthesis from the least substituted aryls appears to be not much studied. In the following study, we focused on the use of less hindered variety of precursors in hexaphyrin and porphyrin synthesis via the Cu(OTf)2-catalyzed reaction of

• ). Intermediates in the reaction mixture of 5 and 2h at 30 min at 0 °C. Retrosynthetic method for A4B2-hexaphyrin and A3B-porphyrin synthesis. A suggested reaction pathway for the formation of A4B2-hexaphyrins and A3B-porphyrins. Synthesis of A3B-porphyrins and A4B2-hexaphyrins. Synthesis of AmBn-type porphyrins

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• literature on meso-substituted triazole-bridging porphyrin synthesis is more than that of β-substituted triazoloporphyrin, therefore, the second section is further divided into five subsections to discuss the synthesis of meso-substituted mono-, di-, tri-, tetra-, and octatriazole-linked porphyrin conjugates

• researchers around the world to use CuAAC and its modifications in various fields of industrial and scientific research, which can be useful in materials to medical and other applications. Alkyne–azide "click reaction". β- and meso-triazole-linked porphyrin. Synthesis of β-triazole-linked porphyrins 3a–c

Extending mechanochemical porphyrin synthesis to bulkier aromatics: tetramesitylporphyrin

• Qiwen Su and
• Tamara D. Hamilton

Beilstein J. Org. Chem. 2019, 15, 1149–1153, doi:10.3762/bjoc.15.111

• -positions have been historically difficult in porphyrin synthesis, presumably owing to steric hindrance around the reactive site. We have used mechanochemistry for the simple, room-temperature synthesis of tetra-meso-substituted porphyrins. In the present study, mesitaldehyde undergoes acid-catalyzed

• mechanochemical condensation with pyrrole to give meso-tetrakis[2,4,6-(trimethyl)phenyl]porphyrin (TMP) after oxidation in solution. Yields are similar to those obtained using high-temperature porphyrin synthesis, although they remain significantly lower than some optimized room-temperature, solution-based

• materials, namely: pyrrole and an aldehyde (Scheme 1). Porphyrin synthesis is interesting to study as a mechanochemical reaction because it involves the combination of reactive molecules under appropriate conditions to give a very stable, aromatic product. Furthermore, depending on the nature of the

Synthesis and spectroscopic properties of β-meso directly linked porphyrin–corrole hybrid compounds

• Baris Temelli and
• Hilal Kalkan

Beilstein J. Org. Chem. 2018, 14, 187–193, doi:10.3762/bjoc.14.13

• electron-donating methoxy substituent (Scheme 3, 4d), which resulted in a mixture of unidentified compounds after the reaction. This might be due to an acid-catalyzed rearrangement of the substituents, called scrambling, which is a common problem in porphyrin synthesis in the reaction of dipyrromethanes

Discrete multiporphyrin pseudorotaxane assemblies from di- and tetravalent porphyrin building blocks

• Mirko Lohse,
• Larissa K. S. von Krbek,
• Sebastian Radunz,
• Suresh Moorthy,
• Christoph A. Schalley and
• Stefan Hecht

Beilstein J. Org. Chem. 2015, 11, 748–762, doi:10.3762/bjoc.11.85

• then converted in dibromide 19 by an Appel reaction. Macrocyclization of 19 with 3,4-dihydroxybenzaldehyde under “pseudo high-dilution” conditions, i.e., slow addition of the two reactants into a solution of Cs2CO3 in DMF at 100 °C provides the corresponding crown ether aldehyde 20. Porphyrin synthesis