Photoredox Catalysis-Enabled Sulfination of Alcohols and Bromides

William P. Carson, Patrick J. Sarver, Noelle S. Goudy, David W.C. MacMillan

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Sulfinates are important lynchpin intermediates in pharmaceutical production; however, their synthesis via photoredox catalysis is challenging because of their facile oxidation. We herein disclose a photocatalytic strategy for the direct conversion of alcohols and alkyl bromides into alkyl sulfinates. These transformations are enabled by the utilization of easily oxidized radical precursors─namely, alcohol N-heterocyclic carbene adducts and N-adamantyl aminosupersilane─that facilitate efficient synthesis of the oxidatively labile sulfinate products. A broad range of functional groups are amenable to the reported transformations, providing rapid access to sulfonamides, sulfonyl halides, sulfones, and sulfonic acids. The utility of these methods is further demonstrated via the late-stage diversification of natural products and drugs into pharmaceutically relevant sulfonamides and “clickable” sulfonyl fluorides. In summary, this work illustrates the potential of novel radical precursors to expand the breadth of photoredox transformations.

Original languageEnglish (US)
Pages (from-to)20767-20774
Number of pages8
JournalJournal of the American Chemical Society
Volume145
Issue number38
DOIs
StatePublished - Sep 27 2023

All Science Journal Classification (ASJC) codes

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

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