An Electrophilic Reagent for the Direct Introduction of the SCF2 PO(OEt)2 Group to Molecules

Angew Chem Int Ed Engl. 2016 Oct 17;55(43):13490-13494. doi: 10.1002/anie.201607231. Epub 2016 Sep 26.

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.

Keywords: difluoromethylthiolation; electrophilic reagents; fluorine; sulfur; synthetic methods.

Publication types

  • Research Support, Non-U.S. Gov't