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Pd-Catalyzed Cross Coupling Strategy for Functional Porphyrin Arrays

[Image: see text] Porphyrin arrays are an important class of compounds to study interporphyrin electronic interactions that are crucial in determining the rates of energy transfer and electron transfer reactions. When the electronic interactions become stronger, porphyrin arrays exhibit significantl...

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Autores principales: Wang, Kaisheng, Osuka, Atsuhiro, Song, Jianxin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7760067/
https://www.ncbi.nlm.nih.gov/pubmed/33376779
http://dx.doi.org/10.1021/acscentsci.0c01300
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author Wang, Kaisheng
Osuka, Atsuhiro
Song, Jianxin
author_facet Wang, Kaisheng
Osuka, Atsuhiro
Song, Jianxin
author_sort Wang, Kaisheng
collection PubMed
description [Image: see text] Porphyrin arrays are an important class of compounds to study interporphyrin electronic interactions that are crucial in determining the rates of energy transfer and electron transfer reactions. When the electronic interactions become stronger, porphyrin arrays exhibit significantly altered optical and electronic properties owing to large oscillator strength and flexible electronic nature of porphyrins. In addition, porphyrins accept various metal cation in their cavities and the interporphyrin interactions depend upon the coordinated metal. With these in the background, porphyrin arrays have been extensively explored as sensors, multielectron catalysts, photodynamic therapy reagents, artificial photosynthetic antenna, nonlinear optical materials, and so on. Here, we review the synthesis of porphyrin arrays by palladium-catalyzed cross-coupling reactions, which are quite effective to construct carbon–carbon bonds and carbon–nitrogen bonds in porphyrin substrates. Palladium-catalyzed cross coupling reactions employed so far are Suzuki–Miyaura coupling reaction, Sonogashira coupling reaction, Buchwald–Hartwig amination, Mizoroki–Heck reaction, Migita–Kosugi–Stille coupling reaction, and so on. In each case, the representative examples and synthetic advantages are discussed.
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spelling pubmed-77600672020-12-28 Pd-Catalyzed Cross Coupling Strategy for Functional Porphyrin Arrays Wang, Kaisheng Osuka, Atsuhiro Song, Jianxin ACS Cent Sci [Image: see text] Porphyrin arrays are an important class of compounds to study interporphyrin electronic interactions that are crucial in determining the rates of energy transfer and electron transfer reactions. When the electronic interactions become stronger, porphyrin arrays exhibit significantly altered optical and electronic properties owing to large oscillator strength and flexible electronic nature of porphyrins. In addition, porphyrins accept various metal cation in their cavities and the interporphyrin interactions depend upon the coordinated metal. With these in the background, porphyrin arrays have been extensively explored as sensors, multielectron catalysts, photodynamic therapy reagents, artificial photosynthetic antenna, nonlinear optical materials, and so on. Here, we review the synthesis of porphyrin arrays by palladium-catalyzed cross-coupling reactions, which are quite effective to construct carbon–carbon bonds and carbon–nitrogen bonds in porphyrin substrates. Palladium-catalyzed cross coupling reactions employed so far are Suzuki–Miyaura coupling reaction, Sonogashira coupling reaction, Buchwald–Hartwig amination, Mizoroki–Heck reaction, Migita–Kosugi–Stille coupling reaction, and so on. In each case, the representative examples and synthetic advantages are discussed. American Chemical Society 2020-11-16 2020-12-23 /pmc/articles/PMC7760067/ /pubmed/33376779 http://dx.doi.org/10.1021/acscentsci.0c01300 Text en © 2020 The Authors. Published by American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Wang, Kaisheng
Osuka, Atsuhiro
Song, Jianxin
Pd-Catalyzed Cross Coupling Strategy for Functional Porphyrin Arrays
title Pd-Catalyzed Cross Coupling Strategy for Functional Porphyrin Arrays
title_full Pd-Catalyzed Cross Coupling Strategy for Functional Porphyrin Arrays
title_fullStr Pd-Catalyzed Cross Coupling Strategy for Functional Porphyrin Arrays
title_full_unstemmed Pd-Catalyzed Cross Coupling Strategy for Functional Porphyrin Arrays
title_short Pd-Catalyzed Cross Coupling Strategy for Functional Porphyrin Arrays
title_sort pd-catalyzed cross coupling strategy for functional porphyrin arrays
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7760067/
https://www.ncbi.nlm.nih.gov/pubmed/33376779
http://dx.doi.org/10.1021/acscentsci.0c01300
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