Nucleophilic H-Phosphites, H-Phosphinates, and H-Phosphine Oxides in Organic Reactions

Abstract P(O)–H compounds like H-phosphites, H-phosphinates, and H-phosphine oxides are widely used as nucleophiles. Herein, their reactions with unsaturated compounds, C–H activation, the Hirao reaction, P–C, P–S, P–O, P–N, and P–F couplings are thoroughly discussed and summarized. This review will focus on their reactions with alkenes, alkynes, enamides, propynoic acids, epoxide, arynes, arenes, quinones, isothiocyanates, diazo compounds, aldehydes, ketones, imines, pyridines, acid derivatives, carbocations, aryl halides, dibromoalkenes, disulfides, thiosulfates, sulfonyl chlorides, iodonium salts, amines, alcohols, and thiols. 1 Introduction 2 Addition to Alkenes/Alkynes 3 Addition to Other Unsaturated Compounds 4 Coupling with Carbocations 5 Phosphorylation of Aryl C–H Bonds 6 Hirao Reaction 7 P–S, P–O, P–N, or P–F Coupling 8 Conclusions