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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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Detalles Bibliográficos
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
Descripción
Sumario: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.