Development of a General Organophosphorus Radical Trap: Deoxyphosphonylation of Alcohols
Noah B. Bissonnette, Niels Bisballe, Andrew V. Tran, James A. Rossi‐Ashton, David W. C. MacMillan
Abstract
Here we report the design of a general, redox-switchable organophosphorus alkyl radical trap that enables the synthesis of a broad range of C( sp 3 )–P(V) modalities. This “plug-and-play” approach relies upon in situ activation of alcohols and O═P(R 2 )H motifs, two broadly available and inexpensive sources of molecular complexity. The mild, photocatalytic deoxygenative strategy described herein allows for the direct conversion of sugars, nucleosides, and complex pharmaceutical architectures to their organophosphorus analogs. This includes the facile incorporation of medicinally relevant phosphonate ester prodrugs.
Topics & Concepts
ChemistryPhosphonateCombinatorial chemistryAlkylProdrugRedoxTrap (plumbing)Organic chemistryBiochemistryEnvironmental engineeringEngineeringRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesChemical Synthesis and Reactions