N-Phosphinoylaminophthalimide: a phosphinoyl radical precursor applied in phosphinoyl-substituted phenanthridine and ketone synthesis

Abstract

A new phosphinoyl radical precursor, N-phosphinoylaminophthalimide (NPAPI), was developed. The precursor exhibits several practical advantages: facile synthesis from commercially available starting materials, cost-effectiveness at scale, and excellent air and moisture stability under ambient storage conditions. Phosphinoyl radical was generated under basic and oxidative conditions, and captured by isonitrile and olefin, yielding phosphinoyl-substituted phenanthridines and α-phosphinoyl ketones, respectively. This methodology enables phosphinoyl radical-mediated operationally simple synthesis of organophosphorus compounds.