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

• Main Authors: Anja Fingerhut, Jorge Vargas-Caporali, Marco Antonio Leyva-Ramírez, Eusebio Juaristi, Svetlana B. Tsogoeva
• Format: Article
• Language: English
• Published: MDPI AG 2019-09-01
• Series: Molecules
• Subjects: non-heme iron-catalysis; peptide-like ligands; enantioselective epoxidation; terminal olefins; hydrogen peroxide oxidant
• Online Access: https://www.mdpi.com/1420-3049/24/17/3182

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.