NBS-mediated elimination of β-keto sulfides to access enones and dienones

Abstract

A novel transformation of β-keto sulfides into enones has been developed. The new method facilitates an NBS-mediated elimination of sulfides to access both enones and dienones. 22 enone products were obtained in moderate to high yields. 4 different dienones were also prepared in 73%–93% yields. 7 different alkylthio motifs have been removed efficiently from β-keto sulfides. We also found that our transformation proceeds well in gram-scale reactions showing no decrease in yield. This methodology is significant in the research and application of sulfides, giving a new pathway to transform β-keto sulfides into enones.