Copper-Catalyzed Selective Defluorinative Sulfuration of Trifluoropropanamides Leading to α-Fluorothioacrylamides

A practical and efficient method for the synthesis of alpha-fluorothioacrylamide was developed from selective defluorinative sulfuration of trifluoropropanamides with disulfides. The N-chelation-assisted copper-catalyzed defluorination and sulfurization reactions feature excellent functional group tolerance and incorporation of both sulfur atoms of disulfides into acrylamides.

Automated summary

A practical and efficient method for synthesizing alpha-fluorothioacrylamide was developed through selective defluorinative sulfuration of trifluoropropanamides with disulfides. The N-chelation-assisted copper-catalyzed defluorination and sulfurization reactions show excellent functional group tolerance and incorporation of both sulfur atoms of disulfides into acrylamides.