The keteniminium ions generated from the protonation of ynamides formed reversible adducts with counter anions and pyridine-N-oxides as well as halogenated solvents. Above 80 °C, the halonium ions selectively undergo a rate-limiting attack by pyridine-N-oxides, leading to (E)-haloenamides in good yields.
S. W. Kim, T. Um and S. Shin, Chem. Commun., 2017, 53, 2733 DOI: 10.1039/C6CC10286G
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