Catalyzed hydroamidation of internal alkynes meet limited success yet. Our proposed SMH pathway provides a different perspective to catalyze hydroamidation of siloxyalkynes, N-silyl-protected ynamides or N-silyl-protected ynamines. Our proposed SMH mechanism can be divided into two steps, the first step is Ag+ promoted proton and silylium ion (TIPS + ) exchange between siloxy-alkyne and amide, which lead to ketene and silyl-imine, the second step is Ag+ catalyzed nucleophilic addition between ketene and silyl-imine, following with a silylium ion migration lead to final product. The hydroamidation of N-silyl-protected ynamines or N-silyl-protected ynamides could be completed through a similar pathway. The protocol of synthesis of ketene (or ketene imines) and silyl-imine have been well documented, which means we can use Ag+ to catalyze ketene (or ketene imines) and silyl-imine to obtain a variety of substituted enamides. The substrate scopes of N-H source may not only be limited in amides, other p-π conjugated system such as 1,2-diazoles, 1,3-diazoles and diazepines may also suitable for this reaction. In SMH pathway, the electron extraction competition between Ag+ and silylium ion (TIPS+) induce every elementary step and lead to final product, which is an important supplement to the silylium ion chemistry.