4.7 Article

S-(Diethyl phosphonodifluoromethyl)Benzenesulfonothioate: A New Reagent for the Synthesis of SCF2PO(OEt)2-containing Molecules

期刊

ADVANCED SYNTHESIS & CATALYSIS
卷 362, 期 4, 页码 760-764

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901454

关键词

Fluorine; sulfur; diethyl phosphonodifluoromethylthiolation reagent; radical pathway; synthetic methodologies

资金

  1. INSA Rouen
  2. Rouen University
  3. CNRS
  4. EFRD
  5. Labex SynOrg [ANR-11-LABX-0029]
  6. Region Normandie (Crunch Network)
  7. Innovation Chimie Carnot (I2 C)
  8. European Research Council (ERC) under the European Union's Horizon 2020 research and innovation program [758710]
  9. Region Normandy

向作者/读者索取更多资源

In this manuscript, the synthesis of an original SCF2PO(OEt)(2)-containing reagent was depicted. Thanks to the unique properties of this newly-designed source, an unprecedented transformation with aldehydes was conducted under radical conditions, offering an access to value-added fluoroalkylthio compounds. Preliminary mechanistic studies were conducted and supported a radical reaction mechanism. Remarkably, thiol and disulfide derivatives turned out to be suitable coupling partners in a transition metal free transformation towards the synthesis of difficult-to-synthesize unsymmetrical disulfides. Finally, the difunctionalization of 4-phenyl-butene was investigated using this reagent.

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