Beilstein J. Org. Chem.2023,19, 1832–1840, doi:10.3762/bjoc.19.135
of porphyrinogen and hexaphyrinogen forms.
Keywords: A4B2-hexaphyrin; A3B-porphyrin; N-tosylimine; Cu(OTf)2 catalysis; HRESI–TOF analysis; Introduction
Porphyrins and expanded porphyrins have found widespread applications in supramolecular chemistry [1][2][3][4]. Expanded porphyrins are utilized as
selective synthesis of expanded porphyrins and their chemistry with regard to their aromaticity and coordination properties. They used meso-aryl-substituted dipyrromethanes and aldehydes in the synthesis of A3B3-type hexaphyrins [13] and 5,10-diaryl-substituted tripyrranes in A4B2-hexaphyrin synthesis [6
provided the A4B2-hexaphyrins 4d–g (Table 1, entries 4–7), with the A4B2-hexaphyrin 4d isolated with 18% yield. The products 4e–g were obtained in 7–10% yield and their formation was corroborated by HRMS spectral analysis (Figures S64–S66 in Supporting Information File 1). In these reactions, the A3B
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Graphical Abstract
Scheme 1:
Retrosynthetic method for A4B2-hexaphyrin and A3B-porphyrin synthesis.