Formal aza-Michael additions to tropone: Addition of diverse aryl- and alkylamines to tricarbonyl(tropone)iron and [(C7H7O)Fe(CO)3]BF4

TETRAHEDRON LETTERS

卷:59

Article

Huang, Zhiyuan¹  Phelan, Zaki K.¹  Tritt, Rachel L.¹  Valent, Shelby D.¹  Griffith, Daniel R.¹ 

[1] Lafayette Coll, Dept Chem, 701 Sullivan Rd, Easton, PA 18042 USA

关键词: Iron diene complexes;    aza-Michael reaction;    Tropone;    Solvent free;   

DOI  :  10.1016/j.tetlet.2018.08.006

来源: Elsevier

【 摘 要 】

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. (C) 2018 Elsevier Ltd. All rights reserved.

【 授权许可】

Free