Yes / Ynamides/arylynamines are challenging substrates for oxyacetoxylation, especially due to various reactive sites of N-heteroaryl ring. Herein we report a metal-free PhI(OAc)2-mediated oxyacetoxylation of arylynamines / ynamides to provide α-acetoxyl amides in good to excellent yields. The transformation completes in a short time to afford solely the product without functionalising N-heteroaryl moiety, in a highly regio- and chemo-selective manner through β-iodo keteneiminium intermediate.