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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...

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Autores principales: Yamada, Tsuyoshi, Teranishi, Wataru, Sakurada, Naoya, Ootori, Seiya, Abe, Yuka, Matsuo, Tomohiro, Morii, Yasuharu, Yoshimura, Masatoshi, Yoshimura, Takeo, Ikawa, Takashi, Sajiki, Hironao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
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.
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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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