An Electrophilic Reagent for the Direct Introduction of the SCF2PO(OEt)2 Group to Molecules
Heng-Ying Xiong
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France
Search for more papers by this authorDr. Alexandre Bayle
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France
Search for more papers by this authorProf. Xavier Pannecoucke
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France
Search for more papers by this authorCorresponding Author
Dr. Tatiana Besset
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France
Search for more papers by this authorHeng-Ying Xiong
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France
Search for more papers by this authorDr. Alexandre Bayle
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France
Search for more papers by this authorProf. Xavier Pannecoucke
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France
Search for more papers by this authorCorresponding Author
Dr. Tatiana Besset
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France
Search for more papers by this authorGraphical Abstract
Tool up: A new electrophilic difluoromethylthiolating reagent (MesNHSCF2PO(OEt)2) was treated with various nucleophiles under mild and metal-free conditions, 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. The versatility of this method was illustrated through the synthesis of the non-stereoidal anti-inflammatory compound diflumidone.
Abstract
An unprecedented electrophilic difluoromethylthiolating reagent (MesNHSCF2PO(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.
Supporting Information
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