Contracted porphyrins and calixpyrroles: synthetic challenges and ring-contraction effects.
| Autor: | Watanabe K; Division of Applied Chemistry, Faculty of Engineering, Hokkaido University Kita 13, Nishi 8 Kita-ku Sapporo Hokkaido 060-8628 Japan inokuma@eng.hokudai.ac.jp., Pati NN; Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University Kita 21, Nishi 10, Kita-ku Sapporo Hokkaido 001-0021 Japan., Inokuma Y; Division of Applied Chemistry, Faculty of Engineering, Hokkaido University Kita 13, Nishi 8 Kita-ku Sapporo Hokkaido 060-8628 Japan inokuma@eng.hokudai.ac.jp.; Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University Kita 21, Nishi 10, Kita-ku Sapporo Hokkaido 001-0021 Japan. |
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| Jazyk: | angličtina |
| Zdroj: | Chemical science [Chem Sci] 2024 Apr 24; Vol. 15 (19), pp. 6994-7009. Date of Electronic Publication: 2024 Apr 24 (Print Publication: 2024). |
| DOI: | 10.1039/d4sc02028f |
| Abstrakt: | Ring-contracted porphyrin analogues, such as subporphyrins and calix[3]pyrroles, have recently attracted considerable attention not only as challenging synthetic targets but also as functional macrocyclic compounds. Although canonical porphyrins and calix[4]pyrrole are selectively generated via acid-catalyzed condensation reactions of pyrrole monomers, their tripyrrolic analogues are always missing under similar conditions. Recent progress in synthesis has shown that strain-controlled approaches using boron(iii)-templating, core-modification, or ring tightening provide access to various contracted porphyrins. The tripyrrolic macrocycles are a new class of functional macrocycles exhibiting unique ring-contraction effects, including strong boron chelation and strain-induced ring expansion. This Perspective reviews recent advances in synthetic strategies and the novel ring-contraction effects of subporphyrins, triphyrins(2.1.1), calix[3]pyrroles, and their analogous. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.) |
| Databáze: | MEDLINE |
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