Silver-Catalyzed Markovnikov Addition Hydrofunctionalization of Terminal Alkynes: Synthesis of N-Enoxyimides and Oximes

N-Enoxyimides are versatile and valuable synthetic synthons in modern organic synthesis and catalysis. Herein, a silver-catalyzed hydrooxyimidation of terminal alkynes that enables the synthesis of N-enoxyimides, has been demonstrated. The protocol features are simple, step- and atom-efficient, scalable, and exhibit a broad scope of functional group tolerance under mild conditions. A novel hydrolysis of the N-enoxyimides unexpectedly provides the corresponding aromatic oximes in 96% yield, showing the potential application of this strategy.