Efficient Synthesis of N-(Difluoropropenyl)amides/Amines from Fluorinated Olefins under Base Promotion

Abstract

Difluoroacrylamides/amines are an important class of fluorinated compounds. Here, we report an efficient synthesis method for difluoroacrylamides without the use of transition metals. Under simple base promoted conditions, 3-bromo-3,3-difluoroprop-1-ene can react with aniline or mono-substituted aniline, removing one molecule of HBr to obtain the target compound. The substituent can be methyl or acryloyl. Another efficient method for synthesizing difluoroalkenes is the reaction of 2-bromo-3,3,3-trifluoroprop-1-ene with indole, which can also yield difluoroalkenes under standard conditions.