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Direct Utilization of Near-Infrared Light for Photooxidation with a Metal-Free Photocatalyst
Near-infrared (NIR) light-triggered photoredox catalysis is highly desirable because NIR light occupies almost 50% of solar energy and possesses excellent penetrating power in various media. Herein we utilize a metal-free boron dipyrromethene (BODIPY) derivative as the photocatalyst to achieve NIR l...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9268673/ https://www.ncbi.nlm.nih.gov/pubmed/35807299 http://dx.doi.org/10.3390/molecules27134047 |
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author | Zeng, Le Wang, Zhonghe Zhang, Tiexin Duan, Chunying |
author_facet | Zeng, Le Wang, Zhonghe Zhang, Tiexin Duan, Chunying |
author_sort | Zeng, Le |
collection | PubMed |
description | Near-infrared (NIR) light-triggered photoredox catalysis is highly desirable because NIR light occupies almost 50% of solar energy and possesses excellent penetrating power in various media. Herein we utilize a metal-free boron dipyrromethene (BODIPY) derivative as the photocatalyst to achieve NIR light (720 nm LED)–driven oxidation of benzylamine derivatives, sulfides, and aryl boronic acids. Compared to blue light–driven photooxidation using Ru(bpy)(3)Cl(2) as a photocatalyst, NIR light–driven photooxidation exhibited solvent independence and superior performance in large-volume (20 mL) reaction, presumably thanks to the neutral structure of a BODIPY photocatalyst and the deeper penetration depth of NIR light. We further demonstrate the application of this metal-free NIR photooxidation to prodrug activation and combination with Cu-catalysis for cross coupling reaction, exhibiting the potential of metal-free NIR photooxidation as a toolbox for organic synthesis and drug development. |
format | Online Article Text |
id | pubmed-9268673 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-92686732022-07-09 Direct Utilization of Near-Infrared Light for Photooxidation with a Metal-Free Photocatalyst Zeng, Le Wang, Zhonghe Zhang, Tiexin Duan, Chunying Molecules Article Near-infrared (NIR) light-triggered photoredox catalysis is highly desirable because NIR light occupies almost 50% of solar energy and possesses excellent penetrating power in various media. Herein we utilize a metal-free boron dipyrromethene (BODIPY) derivative as the photocatalyst to achieve NIR light (720 nm LED)–driven oxidation of benzylamine derivatives, sulfides, and aryl boronic acids. Compared to blue light–driven photooxidation using Ru(bpy)(3)Cl(2) as a photocatalyst, NIR light–driven photooxidation exhibited solvent independence and superior performance in large-volume (20 mL) reaction, presumably thanks to the neutral structure of a BODIPY photocatalyst and the deeper penetration depth of NIR light. We further demonstrate the application of this metal-free NIR photooxidation to prodrug activation and combination with Cu-catalysis for cross coupling reaction, exhibiting the potential of metal-free NIR photooxidation as a toolbox for organic synthesis and drug development. MDPI 2022-06-23 /pmc/articles/PMC9268673/ /pubmed/35807299 http://dx.doi.org/10.3390/molecules27134047 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Zeng, Le Wang, Zhonghe Zhang, Tiexin Duan, Chunying Direct Utilization of Near-Infrared Light for Photooxidation with a Metal-Free Photocatalyst |
title | Direct Utilization of Near-Infrared Light for Photooxidation with a Metal-Free Photocatalyst |
title_full | Direct Utilization of Near-Infrared Light for Photooxidation with a Metal-Free Photocatalyst |
title_fullStr | Direct Utilization of Near-Infrared Light for Photooxidation with a Metal-Free Photocatalyst |
title_full_unstemmed | Direct Utilization of Near-Infrared Light for Photooxidation with a Metal-Free Photocatalyst |
title_short | Direct Utilization of Near-Infrared Light for Photooxidation with a Metal-Free Photocatalyst |
title_sort | direct utilization of near-infrared light for photooxidation with a metal-free photocatalyst |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9268673/ https://www.ncbi.nlm.nih.gov/pubmed/35807299 http://dx.doi.org/10.3390/molecules27134047 |
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