Metal-Free Csp3–N Bond Cleavage of Amides Using tert-Butyl Hydroperoxide as Oxidant

Abstract

A mild and efficient protocol for the metal-free C-N bondcleavage of amides has been developed. The methodology employs iodine as a catalyst to cleave the C(Me)-N bond of dimethylformamide or dimethylacetamide, providing novel access to methylene-bridged bis-1,3-dicarbonyl compounds instead of enol carbamates in the presence of tert-butyl hydroperoxide.