Development of a General Organophosphorus Radical Trap: Deoxyphosphonylation of Alcohols

Here we report the conceptualization and design of a general, redox switchable organophosphorus alkyl radical trap enabling the synthesis of a broad range of C(sp3)–P(V) modalities. This plug-and-play approach relies upon an in-situ activation of alcohols and dialkyl phosphites, two broadly available sources of molecular complexity. The mild, photocatalytic deoxygenative strategy employed here allows for the direct transformation of sugars, nucleosides, and complex pharmaceutical architectures to their organophosphorus analogs, including medicinally relevant phosphonate ester prodrugs.