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Biomimetic Non-Heme Iron-Catalyzed Epoxidation of Challenging Terminal Alkenes Using Aqueous H2O2 as an Environmentally Friendly Oxidant

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Department of Chemistry and Pharmacy, Institute of Organic Chemistry I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander University Erlangen-Nürnberg, Nikolaus-Fiebiger-Straße 10, 91058 Erlangen, Germany
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Department of Chemistry, Centro de Investigación y de Estudios Avanzados, Av. Instituto Politécnico Nacional 2508, 07360 Ciudad de México, Mexico
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El Colegio Nacional, Donceles # 104, Centro Histórico, 06020 Ciudad de México, Mexico
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Authors to whom correspondence should be addressed.
Academic Editor: Isaac Garcia-Bosch
Molecules 2019, 24(17), 3182; https://doi.org/10.3390/molecules24173182
Received: 10 June 2019 / Revised: 20 August 2019 / Accepted: 23 August 2019 / Published: 1 September 2019
Catalysis mediated by iron complexes is emerging as an eco-friendly and inexpensive option in comparison to traditional metal catalysis. The epoxidation of alkenes constitutes an attractive application of iron(III) catalysis, in which terminal olefins are challenging substrates. Herein, we describe our study on the design of biomimetic non-heme ligands for the in situ generation of iron(III) complexes and their evaluation as potential catalysts in epoxidation of terminal olefins. Since it is well-known that active sites of oxidases might involve imidazole fragment of histidine, various simple imidazole derivatives (seven compounds) were initially evaluated in order to find the best reaction conditions and to develop, subsequently, more elaborated amino acid-derived peptide-like chiral ligands (10 derivatives) for enantioselective epoxidations. View Full-Text
Keywords: non-heme iron-catalysis; peptide-like ligands; enantioselective epoxidation; terminal olefins; hydrogen peroxide oxidant non-heme iron-catalysis; peptide-like ligands; enantioselective epoxidation; terminal olefins; hydrogen peroxide oxidant
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MDPI and ACS Style

Fingerhut, A.; Vargas-Caporali, J.; Leyva-Ramírez, M.A.; Juaristi, E.; Tsogoeva, S.B. Biomimetic Non-Heme Iron-Catalyzed Epoxidation of Challenging Terminal Alkenes Using Aqueous H2O2 as an Environmentally Friendly Oxidant. Molecules 2019, 24, 3182.

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