Selective Late-Stage Oxygenation of Sulfides with Ground-State Oxygen by Uranyl Photocatalysis

  • Yiming Li
  • , S. Aal e.Ali Rizvi
  • , Deqing Hu
  • , Danwen Sun
  • , Anhui Gao
  • , Yubo Zhou
  • , Jia Li
  • , Xuefeng Jiang*
  • *Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

220 Scopus citations

Abstract

Oxygenation is a fundamental transformation in synthesis. Herein, we describe the selective late-stage oxygenation of sulfur-containing complex molecules with ground-state oxygen under ambient conditions. The high oxidation potential of the active uranyl cation (UO22+) enabled the efficient synthesis of sulfones. The ligand-to-metal charge transfer process (LMCT) from O 2p to U 5f within the O=U=O group, which generates a UV center and an oxygen radical, is assumed to be affected by the solvent and additives, and can be tuned to promote selective sulfoxidation. This tunable strategy enabled the batch synthesis of 32 pharmaceuticals and analogues by late-stage oxygenation in an atom- and step-efficient manner.

Original languageEnglish
Pages (from-to)13499-13506
Number of pages8
JournalAngewandte Chemie - International Edition
Volume58
Issue number38
DOIs
StatePublished - 16 Sep 2019

Keywords

  • oxygen
  • oxygenation
  • photocatalysis
  • sulfides
  • uranyl catalysis

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