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Ionically Tagged Iron Complex‐Catalyzed Epoxidation of Olefins in Imidazolium‐Based Ionic Liquids

2012; Wiley; Volume: 5; Issue: 4 Linguagem: Inglês

10.1002/cssc.201100453

1864-564X

Marcelo R. dos Santos, Júlia R. Diniz, Aline M. Arouca, Alexandre F. Gomes, Fábio C. Gozzo, S.M. Tamborim, Alexandre Luís Parize, Paulo A. Z. Suarez, Brenno A. D. Neto,

Ionic liquids properties and applications

Abstract A new ionophilic ligand and a new ionically tagged imidazolium‐based iron(III) complex were synthesized and applied in the air oxidation (also hydrogen peroxide) of alkenes in imidazolium‐based ionic liquids. At least ten recycling reactions were performed. The epoxidized olefin was obtained in very good yields of 84–91 %. Some important mechanistic insights are also provided based on electrospray ionization quadrupole–time of flight mass spectrometry for the oxidation reaction. These results indicate that oxidations can take place by two different pathways, depending on the reaction condition: a radical or a concerted mechanism. These results contribute towards a better understanding of iron‐catalyzed oxidation mechanisms.