A metal- and base-free C(sp2)-H direct arylsulfonylation of secondary and tertiary enamides with aryldiazonium salts and ex situ generated SO2 (from SOgen) is presented. This method runs smoothly to produce β-amidovinyl sulfones with excellent stereoselectivities in moderate to excellent yields. Moreover, this strategy features good functional group tolerance and environmentally benign reaction conditions. Mechanistic experiments indicate that this sulfonylation may proceed in a radical pathway.