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

AUTOR(ES)

Cândido, Augusto A.; Rozada, Thiago C.; Rozada, Andrew M. F.; Souza, João R. B.; Pilau, Eduardo J.; Rosa, Fernanda A.; Basso, Ernani A.; Gauze, Gisele F.

FONTE

J. Braz. Chem. Soc.

DATA DE PUBLICAÇÃO

2020-09

RESUMO

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.

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