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

Authors

  • Marcelo R. dos Santos,

    1. Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), 70904-970, P.O.Box 4478, Brasília-DF (Brazil), Fax: (+55) 61-32734149
    2. INCT-Catálise, Departamento de Química, Universidade Federal de Santa Catarina, 88040-900, Florianópolis-SC (Brazil)
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  • Julia R. Diniz,

    1. Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), 70904-970, P.O.Box 4478, Brasília-DF (Brazil), Fax: (+55) 61-32734149
    2. INCT-Catálise, Departamento de Química, Universidade Federal de Santa Catarina, 88040-900, Florianópolis-SC (Brazil)
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  • Aline M. Arouca,

    1. Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), 70904-970, P.O.Box 4478, Brasília-DF (Brazil), Fax: (+55) 61-32734149
    2. INCT-Catálise, Departamento de Química, Universidade Federal de Santa Catarina, 88040-900, Florianópolis-SC (Brazil)
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  • Alexandre F. Gomes,

    1. Institute of Chemistry, State University of Campinas, 13083-970, Campinas-SP (Brazil)
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  • Prof. Dr. Fabio C. Gozzo,

    1. Institute of Chemistry, State University of Campinas, 13083-970, Campinas-SP (Brazil)
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  • Prof. Dr. Silvia M. Tamborim,

    1. Universidade Federal do Pampa, Unipampa, 96412-240, Bagé-RS (Brazil)
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  • Prof. Dr. Alexandre L. Parize,

    1. Laboratório de Materiais e Combustíveis, IQ-UnB, 70910900, Brasília-DF (Brazil)
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  • Prof. Dr. Paulo A. Z. Suarez,

    1. Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), 70904-970, P.O.Box 4478, Brasília-DF (Brazil), Fax: (+55) 61-32734149
    2. INCT-Catálise, Departamento de Química, Universidade Federal de Santa Catarina, 88040-900, Florianópolis-SC (Brazil)
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  • Prof. Dr. Brenno A. D. Neto

    Corresponding author
    1. Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), 70904-970, P.O.Box 4478, Brasília-DF (Brazil), Fax: (+55) 61-32734149
    2. INCT-Catálise, Departamento de Química, Universidade Federal de Santa Catarina, 88040-900, Florianópolis-SC (Brazil)
    • Laboratory of Medicinal and Technological Chemistry, University of Brasília, Chemistry Institute (IQ-UnB), 70904-970, P.O.Box 4478, Brasília-DF (Brazil), Fax: (+55) 61-32734149
    Search for more papers by this author

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.

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