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Microwave-assisted C–C bond formation of diarylacetylenes and aromatic hydrocarbons on carbon beads under continuous-flow conditions
The synthesis of polycyclic aromatic compounds generally requires stoichiometric oxidants or homogeneous metal catalysts, however, the risk of contamination of inorganic residues can affect their properties. Here we present a microwave (MW)-assisted platinum on beaded activated carbon (Pt/CB)-cataly...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10123573/ https://www.ncbi.nlm.nih.gov/pubmed/37095153 http://dx.doi.org/10.1038/s42004-023-00880-y |
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author | Yamada, Tsuyoshi Teranishi, Wataru Sakurada, Naoya Ootori, Seiya Abe, Yuka Matsuo, Tomohiro Morii, Yasuharu Yoshimura, Masatoshi Yoshimura, Takeo Ikawa, Takashi Sajiki, Hironao |
author_facet | Yamada, Tsuyoshi Teranishi, Wataru Sakurada, Naoya Ootori, Seiya Abe, Yuka Matsuo, Tomohiro Morii, Yasuharu Yoshimura, Masatoshi Yoshimura, Takeo Ikawa, Takashi Sajiki, Hironao |
author_sort | Yamada, Tsuyoshi |
collection | PubMed |
description | The synthesis of polycyclic aromatic compounds generally requires stoichiometric oxidants or homogeneous metal catalysts, however, the risk of contamination of inorganic residues can affect their properties. Here we present a microwave (MW)-assisted platinum on beaded activated carbon (Pt/CB)-catalyzed C–C bond formation of diarylacetylenes and aromatic hydrocarbons under continuous-flow conditions. Various fused aromatic compounds were continuously synthesized via dehydrogenative C(sp(2))–C(sp(2)) and C(sp(2))–C(sp(3)) bond formation with yields of up to 87% without the use of oxidants and bases. An activated, local reaction site on Pt/CB in the flow reaction channel reaching temperatures of more than three hundred degrees Celsius was generated in the catalyst cartridge by selective microwave absorption in CB with an absorption efficiency of > 90%. Mechanistic experiments of the transformation reaction indicated that a constant hydrogen gas supply was essential for activating Pt. This is an ideal reaction with minimal input energy and no waste production. |
format | Online Article Text |
id | pubmed-10123573 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-101235732023-04-25 Microwave-assisted C–C bond formation of diarylacetylenes and aromatic hydrocarbons on carbon beads under continuous-flow conditions Yamada, Tsuyoshi Teranishi, Wataru Sakurada, Naoya Ootori, Seiya Abe, Yuka Matsuo, Tomohiro Morii, Yasuharu Yoshimura, Masatoshi Yoshimura, Takeo Ikawa, Takashi Sajiki, Hironao Commun Chem Article The synthesis of polycyclic aromatic compounds generally requires stoichiometric oxidants or homogeneous metal catalysts, however, the risk of contamination of inorganic residues can affect their properties. Here we present a microwave (MW)-assisted platinum on beaded activated carbon (Pt/CB)-catalyzed C–C bond formation of diarylacetylenes and aromatic hydrocarbons under continuous-flow conditions. Various fused aromatic compounds were continuously synthesized via dehydrogenative C(sp(2))–C(sp(2)) and C(sp(2))–C(sp(3)) bond formation with yields of up to 87% without the use of oxidants and bases. An activated, local reaction site on Pt/CB in the flow reaction channel reaching temperatures of more than three hundred degrees Celsius was generated in the catalyst cartridge by selective microwave absorption in CB with an absorption efficiency of > 90%. Mechanistic experiments of the transformation reaction indicated that a constant hydrogen gas supply was essential for activating Pt. This is an ideal reaction with minimal input energy and no waste production. Nature Publishing Group UK 2023-04-24 /pmc/articles/PMC10123573/ /pubmed/37095153 http://dx.doi.org/10.1038/s42004-023-00880-y Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . |
spellingShingle | Article Yamada, Tsuyoshi Teranishi, Wataru Sakurada, Naoya Ootori, Seiya Abe, Yuka Matsuo, Tomohiro Morii, Yasuharu Yoshimura, Masatoshi Yoshimura, Takeo Ikawa, Takashi Sajiki, Hironao Microwave-assisted C–C bond formation of diarylacetylenes and aromatic hydrocarbons on carbon beads under continuous-flow conditions |
title | Microwave-assisted C–C bond formation of diarylacetylenes and aromatic hydrocarbons on carbon beads under continuous-flow conditions |
title_full | Microwave-assisted C–C bond formation of diarylacetylenes and aromatic hydrocarbons on carbon beads under continuous-flow conditions |
title_fullStr | Microwave-assisted C–C bond formation of diarylacetylenes and aromatic hydrocarbons on carbon beads under continuous-flow conditions |
title_full_unstemmed | Microwave-assisted C–C bond formation of diarylacetylenes and aromatic hydrocarbons on carbon beads under continuous-flow conditions |
title_short | Microwave-assisted C–C bond formation of diarylacetylenes and aromatic hydrocarbons on carbon beads under continuous-flow conditions |
title_sort | microwave-assisted c–c bond formation of diarylacetylenes and aromatic hydrocarbons on carbon beads under continuous-flow conditions |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10123573/ https://www.ncbi.nlm.nih.gov/pubmed/37095153 http://dx.doi.org/10.1038/s42004-023-00880-y |
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