This communication describes the synthesis and reactivity of Ni-IV(aryl)(CF3)(2) complexes supported by trispyrazolylborate and 4,4'-di-tert-butylbipyridine ligands. We demonstrate that isolable Ni-IV complexes can be accessed under mild conditions via the oxidation of Ni-II precursors with S-(trifluoromethyl)dibenzothiophenium triflate as well as with diaryliodonium and aryl diazonium reagents. The Ni-IV intermediates undergo high yielding aryl-CF3 bond-forming reductive elimination. These studies support the potential viability of Ni-IV intermediates in nickel-catalyzed coupling reactions involving diaryliodonium and aryldiazonium electrophiles.