Selective Nickel-Catalyzed Hydrodefluorination of Amides Using Sodium Borohydride.

Abstract

Hydrodefluorination selective to the ortho position to amides is accomplished under mild conditions using sodium borohydride and a nickel catalyst. The facile formation of a nickelacycle intermediate with a specific geometry ensures selectivity without the need for electronic directing groups, and fluorine atoms in other positions remain intact. This method avoids the use of stoichiometric silanes which are typical for most other defluorination reactions, resulting in virtually no organic waste byproducts.