Cu-Catalyzed One-Pot Synthesis of Trifluoromethylated β-Lactams by Reaction of Nitrosoarenes, Trifluorodiazoethane and Arylacetylenes

In this paper, we disclose the utility of trifluorodiazoethane in forging trifluoromethylated β-lactams through a streamlined, one-pot Cu-catalyzed reaction involving nitrosoarenes and alkynes. This process involves the in situ generation of trifluoromethylnitrones from trifluorodiazoethane and nitrosoarenes, followed by their reaction with arylacetylenes under Kinugasa conditions, leading to the formation of trifluoromethylated β-lactams. A broad scope of reaction partners, including the Seyferth-Gilbert reagent, various nitrosoarenes, and alkynes, was demonstrated, along with an illustration of the potential of this strategy through multiple synthetic modifications.