Gram-scale synthesis of porphycenes through acid-catalyzed oxidative macrocyclizations of E/Z-mixed 5,6-diaryldipyrroethenes

The gram-scale production of porphycene derivatives is reported. This has been achieved by acid-catalyzed ring closure of an E/Z-mixture of 5,6-diaryldipyrroethenes, resulting in the formation of meso-tetraarylporphycenes in yields of up to 80%. E/Z-isomerization of the 5,6-diaryldipyrroethenes unde...

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Autores principales: Ono, Toshikazu, Xu, Ning, Koga, Daiki, Ideo, Toshihiro, Sugimoto, Manabu, Hisaeda, Yoshio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9090978/
https://www.ncbi.nlm.nih.gov/pubmed/35558012
http://dx.doi.org/10.1039/c8ra09040h
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author Ono, Toshikazu
Xu, Ning
Koga, Daiki
Ideo, Toshihiro
Sugimoto, Manabu
Hisaeda, Yoshio
author_facet Ono, Toshikazu
Xu, Ning
Koga, Daiki
Ideo, Toshihiro
Sugimoto, Manabu
Hisaeda, Yoshio
author_sort Ono, Toshikazu
collection PubMed
description The gram-scale production of porphycene derivatives is reported. This has been achieved by acid-catalyzed ring closure of an E/Z-mixture of 5,6-diaryldipyrroethenes, resulting in the formation of meso-tetraarylporphycenes in yields of up to 80%. E/Z-isomerization of the 5,6-diaryldipyrroethenes under acidic conditions was key to proceed the effective macrocyclization.
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spelling pubmed-90909782022-05-11 Gram-scale synthesis of porphycenes through acid-catalyzed oxidative macrocyclizations of E/Z-mixed 5,6-diaryldipyrroethenes Ono, Toshikazu Xu, Ning Koga, Daiki Ideo, Toshihiro Sugimoto, Manabu Hisaeda, Yoshio RSC Adv Chemistry The gram-scale production of porphycene derivatives is reported. This has been achieved by acid-catalyzed ring closure of an E/Z-mixture of 5,6-diaryldipyrroethenes, resulting in the formation of meso-tetraarylporphycenes in yields of up to 80%. E/Z-isomerization of the 5,6-diaryldipyrroethenes under acidic conditions was key to proceed the effective macrocyclization. The Royal Society of Chemistry 2018-11-26 /pmc/articles/PMC9090978/ /pubmed/35558012 http://dx.doi.org/10.1039/c8ra09040h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Ono, Toshikazu
Xu, Ning
Koga, Daiki
Ideo, Toshihiro
Sugimoto, Manabu
Hisaeda, Yoshio
Gram-scale synthesis of porphycenes through acid-catalyzed oxidative macrocyclizations of E/Z-mixed 5,6-diaryldipyrroethenes
title Gram-scale synthesis of porphycenes through acid-catalyzed oxidative macrocyclizations of E/Z-mixed 5,6-diaryldipyrroethenes
title_full Gram-scale synthesis of porphycenes through acid-catalyzed oxidative macrocyclizations of E/Z-mixed 5,6-diaryldipyrroethenes
title_fullStr Gram-scale synthesis of porphycenes through acid-catalyzed oxidative macrocyclizations of E/Z-mixed 5,6-diaryldipyrroethenes
title_full_unstemmed Gram-scale synthesis of porphycenes through acid-catalyzed oxidative macrocyclizations of E/Z-mixed 5,6-diaryldipyrroethenes
title_short Gram-scale synthesis of porphycenes through acid-catalyzed oxidative macrocyclizations of E/Z-mixed 5,6-diaryldipyrroethenes
title_sort gram-scale synthesis of porphycenes through acid-catalyzed oxidative macrocyclizations of e/z-mixed 5,6-diaryldipyrroethenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9090978/
https://www.ncbi.nlm.nih.gov/pubmed/35558012
http://dx.doi.org/10.1039/c8ra09040h
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