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

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

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(sp3)-P(V) modalities. This “plug-and-play” approach relies upon in situ activation of alcohols and O═P(R2)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.

Original languageEnglish (US)
Pages (from-to)7942-7949
Number of pages8
JournalJournal of the American Chemical Society
Volume146
Issue number12
DOIs
StatePublished - Mar 27 2024

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • Biochemistry
  • Catalysis
  • Colloid and Surface Chemistry

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