4.8 Article

An Electrophilic Reagent for the Direct Introduction of the SCF2PO(OEt)2 Group to Molecules

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 43, Pages 13490-13494

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201607231

Keywords

electrophilic reagents; fluorine; sulfur; synthetic methods; difluoromethylthiolation

Funding

  1. INSA Rouen
  2. Rouen University
  3. CNRS
  4. EFRD
  5. Labex SynOrg [ANR-11-LABX-0029]
  6. Region Haute-Normandie (Crunch Network)
  7. CSC (China Scholarship Council)

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An unprecedented electrophilic difluoromethylthiolating reagent (MesNHSCF(2)PO(OEt)(2)) was designed. Under mild and metal-free conditions, this new reagent reacted with various nucleophiles, thus offering an efficient and operationally simple tool for the construction of C-SCF2PO(OR)(2), N-SCF2PO(OR)(2), and S-SCF2PO(OR)(2) bonds. Finally, thanks to this new methodology, the synthesis of the non-stereoidal anti-inflammatory diflumidone was achieved.

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