An Electrophilic Reagent for the Direct Introduction of the SCF2PO(OEt)2 Group to Molecules. Issue 43 (26th September 2016)

• Record Type: Journal Article
• Authors: Xiong, Heng‐Ying; Bayle, Alexandre; Pannecoucke, Xavier; Besset, Tatiana
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 43(2016)
• Page Start: 13490
• Page End: 13494
• Publication Date: 2016-09-26
• Subjects: electrophilic reagents -- fluorine -- sulfur -- synthetic methods -- difluoromethylthiolation; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201607231
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: An unprecedented electrophilic difluoromethylthiolating reagent (MesNHSCF2 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−SCF2 PO(OR)2, N−SCF2 PO(OR)2, and S−SCF2 PO(OR)2 bonds. Finally, thanks to this new methodology, the synthesis of the non‐stereoidal anti‐inflammatory diflumidone was achieved. Abstract : Tool up : A new electrophilic difluoromethylthiolating reagent (MesNHSCF2 PO(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−SCF2 PO(OR)2, N−SCF2 PO(OR)2, and S−SCF2 PO(OR)2 bonds. The versatility of this method was illustrated through the synthesis of the non‐stereoidal anti‐inflammatory compound diflumidone.