Formal aza-Michael additions to tropone: Addition of diverse aryl- and alkylamines to tricarbonyl(tropone)iron and [(C7H7O)Fe(CO)3]BF4
| Autor: | Zhiyuan Huang, Rachel L. Tritt, Shelby D. Valent, Zaki K. Phelan, Daniel R. Griffith |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Tetrafluoroborate
010405 organic chemistry Chemistry Aryl Organic Chemistry Cationic polymerization Protonation 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Adduct chemistry.chemical_compound Nucleophile Drug Discovery Amine gas treating Tropone |
| Zdroj: | Tetrahedron Letters. 59:3432-3434 |
| ISSN: | 0040-4039 |
| DOI: | 10.1016/j.tetlet.2018.08.006 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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