Microwave-assisted C–C bond formation of diarylacetylenes and aromatic hydrocarbons on carbon beads under continuous-flow conditions
Abstract 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/C...
| Main Authors: | , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2023-04-01
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| Series: | Communications Chemistry |
| Online Access: | https://doi.org/10.1038/s42004-023-00880-y |
| _version_ | 1797836580925210624 |
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| author | Tsuyoshi Yamada Wataru Teranishi Naoya Sakurada Seiya Ootori Yuka Abe Tomohiro Matsuo Yasuharu Morii Masatoshi Yoshimura Takeo Yoshimura Takashi Ikawa Hironao Sajiki |
| author_facet | Tsuyoshi Yamada Wataru Teranishi Naoya Sakurada Seiya Ootori Yuka Abe Tomohiro Matsuo Yasuharu Morii Masatoshi Yoshimura Takeo Yoshimura Takashi Ikawa Hironao Sajiki |
| author_sort | Tsuyoshi Yamada |
| collection | DOAJ |
| description | Abstract 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(sp2)–C(sp2) and C(sp2)–C(sp3) 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. |
| first_indexed | 2024-04-09T15:12:19Z |
| format | Article |
| id | doaj.art-e174a2ded8a14dee8f26680546f4d14b |
| institution | Directory Open Access Journal |
| issn | 2399-3669 |
| language | English |
| last_indexed | 2024-04-09T15:12:19Z |
| publishDate | 2023-04-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Communications Chemistry |
| spelling | doaj.art-e174a2ded8a14dee8f26680546f4d14b2023-04-30T11:09:55ZengNature PortfolioCommunications Chemistry2399-36692023-04-016111110.1038/s42004-023-00880-yMicrowave-assisted C–C bond formation of diarylacetylenes and aromatic hydrocarbons on carbon beads under continuous-flow conditionsTsuyoshi Yamada0Wataru Teranishi1Naoya Sakurada2Seiya Ootori3Yuka Abe4Tomohiro Matsuo5Yasuharu Morii6Masatoshi Yoshimura7Takeo Yoshimura8Takashi Ikawa9Hironao Sajiki10Laboratory of Organic Chemistry, Gifu Pharmaceutical University 1-25-4 Daigaku-Nishi, GifuLaboratory of Organic Chemistry, Gifu Pharmaceutical University 1-25-4 Daigaku-Nishi, GifuLaboratory of Organic Chemistry, Gifu Pharmaceutical University 1-25-4 Daigaku-Nishi, GifuLaboratory of Organic Chemistry, Gifu Pharmaceutical University 1-25-4 Daigaku-Nishi, GifuLaboratory of Organic Chemistry, Gifu Pharmaceutical University 1-25-4 Daigaku-Nishi, GifuLaboratory of Organic Chemistry, Gifu Pharmaceutical University 1-25-4 Daigaku-Nishi, GifuProduct Division, Tokyo Rikakikai Co., Ltd. (Brand: EYELA)R&D Center, N.E. Chemcat CorporationSAIDA FDS INC.Laboratory of Organic Chemistry, Gifu Pharmaceutical University 1-25-4 Daigaku-Nishi, GifuLaboratory of Organic Chemistry, Gifu Pharmaceutical University 1-25-4 Daigaku-Nishi, GifuAbstract 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(sp2)–C(sp2) and C(sp2)–C(sp3) 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.https://doi.org/10.1038/s42004-023-00880-y |
| spellingShingle | Tsuyoshi Yamada Wataru Teranishi Naoya Sakurada Seiya Ootori Yuka Abe Tomohiro Matsuo Yasuharu Morii Masatoshi Yoshimura Takeo Yoshimura Takashi Ikawa Hironao Sajiki Microwave-assisted C–C bond formation of diarylacetylenes and aromatic hydrocarbons on carbon beads under continuous-flow conditions Communications Chemistry |
| 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 |
| url | https://doi.org/10.1038/s42004-023-00880-y |
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