Mechanistic Investigation of DBU-Based Ionic Liquids for Aza-Michael Reaction: Mass Spectrometry and DFT Studies of Catalyst Role

Mechanistic Investigation of DBU-Based Ionic Liquids for Aza-Michael Reaction: Mass Spectrometry and DFT Studies of Catalyst Role

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 aroma...

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Hauptverfasser: Cândido, Augusto A., Thiago C. Rozada, Rozada, Andrew M. F., Souza, João R. B., Pilau, Eduardo J., Rosa, Fernanda A., Basso, Ernani A., Gisele F. Gauze
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creator Cândido, Augusto A.
Thiago C. Rozada
Rozada, Andrew M. F.
Souza, João R. B.
Pilau, Eduardo J.
Rosa, Fernanda A.
Basso, Ernani A.
Gisele F. Gauze
description 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.
doi_str_mv 10.6084/m9.figshare.14303942
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Rozada ; Rozada, Andrew M. F. ; Souza, João R. B. ; Pilau, Eduardo J. ; Rosa, Fernanda A. ; Basso, Ernani A. ; Gisele F. Gauze</creator><creatorcontrib>Cândido, Augusto A. ; Thiago C. Rozada ; Rozada, Andrew M. F. ; Souza, João R. B. ; Pilau, Eduardo J. ; Rosa, Fernanda A. ; Basso, Ernani A. ; Gisele F. Gauze</creatorcontrib><description>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. 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title Mechanistic Investigation of DBU-Based Ionic Liquids for Aza-Michael Reaction: Mass Spectrometry and DFT Studies of Catalyst Role
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