Efficient C(sp3)–P(v) bond cleavage and reconstruction of free α-aminophosphonates via palladium catalysis

Abstract

Transition metal-catalyzed cleavage and reconstruction of the C–P bond provides a highly efficient and rapid method for the transformation of organophosphine compounds. In this study, a novel and general protocol for the palladium-catalyzed C(sp³)–P(V) bond cleavage of free α-aminophosphonates and subsequent functionalization via C–P bond recombination has been developed. The reaction exhibits high reactivity between the C(sp³)–P bond and halides, accommodating a wide range of substrates and enabling the rapid synthesis of aryl, alkenyl, and alkyl organophosphine molecules. Additionally, the synthetic utility is validated by gram-scale synthesis, and the reaction process is corroborated by mechanistic experiments.