A Protocol for the Synthesis of Organophosphorus(V) Compounds with P–N and P–O Bonds by Umpolung Strategy Using Hydroxymethylphosphine Sulfides

Versatile P–N and P–O bond-forming reactions by an umpolung approach using air- and moisture-stable hydroxymethylphosphine sulfides were developed. Phosphine sulfides containing multiple hydroxymethyl groups could undergo sequential transformations combining P–N and P–O as well as P–C bond formations, providing a novel protocol for the synthesis of a variety of organophosphorus(V) compounds with P–N and P–O bonds.