H-phosphinates, H-phosphonates and secondary phosphine oxides in radical reactions and strategy analysis

Abstract

Abstract P(O)-H compounds like H-phosphonates, H-phosphinates and secondary phosphine oxides are widely used in radical reactions. Their great successes are rooted in the facile homolytic cleavage of P-H bond. Herein, recent advances of these compounds were summarized as five pathways according to their mechanisms: (1) radical addition and cyclization; (2) cyclization and ring-opening; (3) radical addition and coupling; (4) radical addition and elimination; (5) coupling with nucleophilic partners (C-H, N-H, O-H and S-H). Reactions with alkenes, alkynes, isocyanides, cinnamic acids, propiolic acids, azides, arenes amines, alcohols or thioalcohols will be discussed. We hope this review will do help for future research in this area.