Isolation of Phlorin‐Dipyrrin Conjugates from the Acid‐Catalyzed Condensation of Dipyrromethanes and Aldehydes

Gryko, Daniel T.; Koszarna, Beata

doi:10.1002/ejoc.200500089

Cited by 17 publications

(15 citation statements)

References 43 publications

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“…While a high concentration of TFA and a low concentration of reagents favors formation of porphyrin, the use of a high concentration of substrates and low concentration of TFA is essential to maximize the yield of corrole. , It should be pointed out that in analogy to the condensation of pyrrole with aldehydes, the condensation of dipyrranes with aldehydes is also an unstoppable cascade. Higher oligocondensates form as well, such as oxidation of the product of [3 + 2] condensation that leads to phlorin, which often accompanies trans -A 2 B-corroles …”

Section: Meso-substituted Trans-a2b-corrolesmentioning

confidence: 99%

Synthesis of Corroles and Their Heteroanalogs

2016

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Corroles have come a long way from being a curiosity to being a mainstream research topic. They are now regularly synthesized in numerous research laboratories worldwide with diverse specific aims in mind. In this review we present a comprehensive description of corroles' synthesis, developed both before and after 1999. To aid the investigator in developing synthetic strategies, some of the sections culminate in tables containing comparisons of various methodologies leading to meso-substituted corroles. The remaining challenges are delineated. In the second part of this review, we also describe the syntheses of isocorroles and heteroanalogs of corroles such as triazacorroles (corrolazines), 10-heterocorroles, 21-heterocorroles, 22-heterocorroles, N-confused corroles, as well as norcorroles. The review is complemented with a short outlook.

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Section: Meso-substituted Trans-a2b-corrolesmentioning

confidence: 99%

Synthesis of Corroles and Their Heteroanalogs

2016

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“…Thezinc porphyrin is generated in about 12 %i na ll cases.A ssuming the initial formation of linear oligopyrroles during the condensation step, [21] this study shows,t hat 1) the presence of the acetate salts disturbs the condensation to linear oligopyrroles,a nd 2) the linear penta-and hexapyrrolic intermediates form metal chelates after (partial) dehydrogenation, which favor oxidative ring closure to isoporphyrins rather than to sapphyrins and other expanded porphyrins (Scheme 2). It should be mentioned that the formation of pyrrolyl-or dipyrrinylsubstituted porphyrins, [19a,22] chlorins,a nd phlorins [17,23] from linear penta-and hexapyrroles has occasionally been reported in the past.…”

Section: Angewandte Chemiementioning

confidence: 99%

Metal‐Assisted One‐Pot Synthesis of Isoporphyrin Complexes

et al. 2016

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Zinc and cadmium complexes of meso-arylisoporphyrins carrying a pyrrolyl or dipyrrinyl substituent at the sp(3) carbon atom were obtained through a simple one-pot variation of the Alder-Longo porphyrin synthesis. Key to the formation and stabilization of isoporphyrins is the presence of metal acetates during the oxidative macrocyclization step. The characteristic Q-bands of isoporphyrins are found in the NIR region between 750 nm and 880 nm. All of the isolated pyrrolyl- and dipyrrinyl-appended isoporphyrins are stable under typical laboratory conditions and allow chemical transformations like BF2 coordination, transmetalation, and ligand exchange.

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“…The pentafluorobenzaldehyde has been applied in research of new materials in porphyrin chemistry [111,184,, chemistry of corroles (58 [442][443][444][445][446][447][448][449][450][451][452][453][454][455]), porphocyanines (60) and their precursors (59 [456][457][458][459][460][461] of porphyrins (61), which are utilizable in many fields of chemistry (Scheme 38 [348,[462][463][464][465][466][467]). Along this line, the synthesis of expanded porphyrin cyclescalixphyrines is interesting too (62, Scheme 39 [468][469][470]).…”

Section: Chemical Reactions Of Pentafluorobenzaldehyde With Carbon Numentioning

confidence: 99%