Blue LED-Mediated Syntheses of Arylazo Phosphine Oxides and Phosphonates via N-P Bond Formation

Org Lett. 2022 Aug 19;24(32):5988-5993. doi: 10.1021/acs.orglett.2c02251. Epub 2022 Aug 4.

Abstract

The synthesis of (E)-diphenyl(aryldiazenyl)phosphine oxides and dialkyl (E)-(aryldiazenyl)phosphonates via visible light-mediated N-P bond formation between diazo species and phosphine oxides and phosphite derivatives, respectively, is described. The diazo species were generated via the reaction of aniline with isoamyl nitrite, which upon reaction with phosphorus surrogates generated arylazophosphine oxides and arylazo phosphonates in good to excellent yields. This sustainable chemical process offers a broad substrate scope and reasonably viable product formation.