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Formal aza-Michael additions to tropone: Addition of diverse aryl- and alkylamines to tricarbonyl(tropone)iron and [(C7H7O)Fe(CO)3]BF4
Authors:Zhiyuan Huang  Zaki K Phelan  Rachel L Tritt  Shelby D Valent  Daniel R Griffith
Institution:Department of Chemistry, Lafayette College, 701 Sullivan Road, Easton, PA 18042, USA
Abstract:A formal aza-Michael addition to tropone by way of tricarbonyl(tropone)iron and/or the tetrafluoroborate salt formed via protonation of the complex is reported. Tricarbonyl(tropone)iron smoothly undergoes the direct aza-Michael reaction with unhindered aliphatic amines under solvent free conditions in good yields. Meanwhile, the known cationic complex (C7H7O)Fe(CO)3]BF4 (whose reaction with a small number of nucleophiles was previously reported) undergoes addition with an even broader array of amine nucleophiles. Finally, it was discovered that protecting the aza-Michael adduct as a carbamate was necessary for oxidative demetallation of the complex.
Keywords:Iron diene complexes  Tropone  Solvent free
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