EN300-101508

Reagent for electrophilic aminations and N-deletion in amines

DPPH (O-diphenylphosphinyl hydroxylamine) is an electrophilic amination reagent that occupies a unique niche in organic synthesis. It is a solid, bench-stabile for a year compound with very low solubility in aprotic organic solvents[1]. This reagent rapidly reacts with the NH group in imidazoles, xanthines, indoles, and carbazoles. The usage of DPPH is a reliable method for N-amination of many primary and secondary amines[2], [3] that starts with deprotonation (e.g. with NaH) followed by further treatment with the reagent. Stabilized carbanions or Grignard reagents can serve as substrates for reaction as well[1], [2]. The newly developed methodology allows nitrogen deletion with the DPPH from secondary amines[4]. This reaction demonstrates high functional tolerance and can be applied to α-primary, α-secondary, and α-tertary alkylamines.