1,2-Diarylation of alkenyl sulfonamides with aryl iodides and aryl boronic esters under nickel catalysis is reported. The developed method tolerates coupling partners with disparate electronic properties and substitution patterns. 1,2- and 1,1-Disubstituted alkenes, as well as alkenes distal from the directing group, are all accommodated. Control experiments are consistent with a N–Ni coordination mode of the directing group, which stands in contrast to earlier reports on amide-directed 1,2-diarylation that involve carbonyl coordination. The synthetic utility of the method arises from the dual function of the sulfonamide as both a directing group and masked amine nucleophile. This is highlighted by various product diversifications where complex amine compounds are synthesized in a two-step sequence of N-functionalization and deprotection of the sulfonyl group.