Mechanistic Investigation of DBU-Based Ionic Liquids for Aza-Michael Reaction: Mass Spectrometry and DFT Studies of Catalyst Role
| Autor: | Eduardo Jorge Pilau, Fernanda A. Rosa, Gisele F. Gauze, Thiago C. Rozada, João Raul B. de Souza, Augusto A. Cândido, Ernani A. Basso, Andrew M.F. Rozada |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
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| Zdroj: | Journal of the Brazilian Chemical Society, Volume: 31, Issue: 9, Pages: 1796-1804, Published: 19 AUG 2020 Journal of the Brazilian Chemical Society v.31 n.9 2020 Journal of the Brazilian Chemical Society Sociedade Brasileira de Química (SBQ) instacron:SBQ |
| Popis: | 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-based ionic liquids (ILs) has exhibited a high catalytic activity in the aza-Michael reactions compared to conventional catalysts and with imidazole-based ILs. In the present work DBU-based ILs showed high catalytic potential for aza-Michael addition of aromatic amines to 2-cyclohexen-1-one under solvent-free condition. Electrospray ionization-mass spectrometry (ESI-MS) and density functional theory studies have been carried out to provide an effective activation mode of DBU-based ILs in aza-Michael addition. Our results show that both the presence of the acid hydrogen in the IL and the ability of the anion to carry out a hydrogen bond with the −NH2 group of the arylamine are fundamental for the reaction catalysis. The catalytic model proposed can be used for the rational development of new ILs with excellent catalytic properties. |
| Databáze: | OpenAIRE |
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