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Sulfonylation of Pyridyl Phosphonium Salts with Sulfinate Salts in Aqueous Media for the Synthesis of 4-Pyridyl Sulfones via C-P Bond Cleavage.

Author information

Affiliations

  • 1. Technical Institute of Fluorochemistry (TIF), School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
      Authors
    • Huo BJ 1
    • Wang WW 1
    • Huang YJ 1
    • Chu XQ 1
    • Xu H 1
    • Zhou X 1
    • Shen ZL 1
    (7 authors)
  • 2. Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.
      Authors
    • Rao W 2
    (1 author)

ORCIDs linked to this article

Organic Letters, 30 Aug 2024, 26(36):7763-7768
https://doi.org/10.1021/acs.orglett.4c02922 PMID: 39213616 

Abstract 

A Na2S2O8-initiated sulfonylation of pyridyl phosphonium salts with sulfinate salts in aqueous media has been developed for facile access to 4-pyridyl sulfones. The reactions, which employed pyridyl phosphonium salts as efficient pyridylation agents via C-P bond activation, showed both broad substrate generality and good functional group compatibility. In addition, the scale-up synthesis and the late-stage modification of pharmaceutically active complex molecules (e.g., loratadine, bisacodyl) could also be successfully realized.

Full text links 

Read article at publisher's site: https://doi.org/10.1021/acs.orglett.4c02922

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Funding 

Funders who supported this work.

Nanjing Tech University (2)