Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2-Vinyl Anilines
| Autor: | Tom Wirtanen, Mikko K. Mäkelä, Juho Helaja, Martin Nieger, Tao Hu, Kiia Malinen, Anna Lenarda, Michele Melchionna, Juulia Talvitie, Evgeny Bulatov |
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| Přispěvatelé: | Makela, M. K., Bulatov, E., Malinen, K., Talvitie, J., Nieger, M., Melchionna, M., Lenarda, A., Hu, T., Wirtanen, T., Helaja, J., Department of Chemistry, Doctoral Programme in Chemistry and Molecular Sciences, Helsinki Institute of Sustainability Science (HELSUS), Juho Pekka Helaja / Principal Investigator |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
MECHANISM
Carbocatalysi Carbocatalysis Electrocyclization Oxidative Dehydrogenation Quinoline 116 Chemical sciences EFFICIENT 010402 general chemistry 01 natural sciences C c coupling chemistry.chemical_compound CHEMISTRY medicine Dehydrogenation ACTIVATED CARBON OXIDATIVE AROMATIZATION 010405 organic chemistry Chemistry AMINES General Chemistry Combinatorial chemistry MICHAEL ADDITION 0104 chemical sciences Cascade Michael reaction GRAPHENE OXIDE Density functional theory DEHYDROGENATION SYSTEM Activated carbon medicine.drug |
| Popis: | Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The mechanistic studies imply that both the acid and quinoidic groups in oAC are integral for the catalytic manifold. (Figure presented.). |
| Databáze: | OpenAIRE |
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