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Ceramic boron carbonitrides for unlocking organic halides with visible light
Photochemistry provides a sustainable pathway for organic transformations by inducing radical intermediates from substrates through electron transfer process. However, progress is limited by heterogeneous photocatalysts that are required to be efficient, stable, and inexpensive for long-term operati...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8115245/ https://www.ncbi.nlm.nih.gov/pubmed/34084430 http://dx.doi.org/10.1039/d1sc01028j |
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author | Yuan, Tao Zheng, Meifang Antonietti, Markus Wang, Xinchen |
author_facet | Yuan, Tao Zheng, Meifang Antonietti, Markus Wang, Xinchen |
author_sort | Yuan, Tao |
collection | PubMed |
description | Photochemistry provides a sustainable pathway for organic transformations by inducing radical intermediates from substrates through electron transfer process. However, progress is limited by heterogeneous photocatalysts that are required to be efficient, stable, and inexpensive for long-term operation with easy recyclability and product separation. Here, we report that boron carbonitride (BCN) ceramics are such a system and can reduce organic halides, including (het)aryl and alkyl halides, with visible light irradiation. Cross-coupling of halides to afford new C–H, C–C, and C–S bonds can proceed at ambient reaction conditions. Hydrogen, (het)aryl, and sulfonyl groups were introduced into the arenes and heteroarenes at the designed positions by means of mesolytic C–X (carbon–halogen) bond cleavage in the absence of any metal-based catalysts or ligands. BCN can be used not only for half reactions, like reduction reactions with a sacrificial agent, but also redox reactions through oxidative and reductive interfacial electron transfer. The BCN photocatalyst shows tolerance to different substituents and conserved activity after five recycles. The apparent metal-free system opens new opportunities for a wide range of organic catalysts using light energy and sustainable materials, which are metal-free, inexpensive and stable. |
format | Online Article Text |
id | pubmed-8115245 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81152452021-06-02 Ceramic boron carbonitrides for unlocking organic halides with visible light Yuan, Tao Zheng, Meifang Antonietti, Markus Wang, Xinchen Chem Sci Chemistry Photochemistry provides a sustainable pathway for organic transformations by inducing radical intermediates from substrates through electron transfer process. However, progress is limited by heterogeneous photocatalysts that are required to be efficient, stable, and inexpensive for long-term operation with easy recyclability and product separation. Here, we report that boron carbonitride (BCN) ceramics are such a system and can reduce organic halides, including (het)aryl and alkyl halides, with visible light irradiation. Cross-coupling of halides to afford new C–H, C–C, and C–S bonds can proceed at ambient reaction conditions. Hydrogen, (het)aryl, and sulfonyl groups were introduced into the arenes and heteroarenes at the designed positions by means of mesolytic C–X (carbon–halogen) bond cleavage in the absence of any metal-based catalysts or ligands. BCN can be used not only for half reactions, like reduction reactions with a sacrificial agent, but also redox reactions through oxidative and reductive interfacial electron transfer. The BCN photocatalyst shows tolerance to different substituents and conserved activity after five recycles. The apparent metal-free system opens new opportunities for a wide range of organic catalysts using light energy and sustainable materials, which are metal-free, inexpensive and stable. The Royal Society of Chemistry 2021-03-23 /pmc/articles/PMC8115245/ /pubmed/34084430 http://dx.doi.org/10.1039/d1sc01028j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Yuan, Tao Zheng, Meifang Antonietti, Markus Wang, Xinchen Ceramic boron carbonitrides for unlocking organic halides with visible light |
title | Ceramic boron carbonitrides for unlocking organic halides with visible light |
title_full | Ceramic boron carbonitrides for unlocking organic halides with visible light |
title_fullStr | Ceramic boron carbonitrides for unlocking organic halides with visible light |
title_full_unstemmed | Ceramic boron carbonitrides for unlocking organic halides with visible light |
title_short | Ceramic boron carbonitrides for unlocking organic halides with visible light |
title_sort | ceramic boron carbonitrides for unlocking organic halides with visible light |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8115245/ https://www.ncbi.nlm.nih.gov/pubmed/34084430 http://dx.doi.org/10.1039/d1sc01028j |
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