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

Abstract
A substituent-dependent construction of novel A3B-porphyrins along with A4B2-hexaphyrins was realized by the reactions of N-tosylimines and meso-aryl-substituted tripyrranes in the presence of Cu(OTf)2 as the catalyst. The reaction mechanism of the presented method was studied on model reactions by electrospray-ionization time-of-flight (HRESI–TOF) mass spectral analysis in a timely manner. The analytical results indicated that the observed azafulvene-ended di- and tripyrrolic intermediates are responsible for the formation of porphyrinogen and hexaphyrinogen forms.

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

Source: Beilstein Journal of Organic Chemistry - December 6, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: A4B2-hexaphyrin A3B-porphyrin N-tosylimine Cu(OTf)2 catalysis HRESI – TOF analysis Full Research Paper Source Type: research