Synthesis of α,α-Difluoromethylene Amines from Thioamides Using Silver Fluoride

J Org Chem. 2024 Oct 4;89(19):14341-14347. doi: 10.1021/acs.joc.4c01752. Epub 2024 Sep 18.

Abstract

We developed a mild, rapid process employing AgF and thioamides to produce α,α-difluoromethylene amines efficiently. This method exhibited remarkable tolerance toward various functional groups present in N-sulfonylthioamides, thereby broadening the scope of difluoromethylene sulfonamides through a straightforward approach. Additionally, we applied this approach to synthesize various perfluoroalkyl amines, establishing practical synthetic routes for exploring these compounds in pharmaceutical chemistry and materials science.