This report describes the preparation, characterization, and reactivities of a new family of Ni(II) complexes based on the pincer-type ligands R-NCN pz (κ N ,κ C ,κ N′ -1,3-bis(pyrazole),5-R-C 6 H 2 ; R = H, OMe). Ullman coupling of pyrazole with 1,3diiodobenzene or 1,3-dibromo-5-methoxybenzene gave the compounds R-NC(H)N pz , which were refluxed in xylene with (i-PrCN)NiBr 2 and NEt 3 to give the complexes (NCN pz )NiBr ( 1) and (MeO-NCN pz )NiBr (2) via C−H nickelation. The aryloxide derivative (NCN pz )Ni(OAr) (3; Ar = 2,6-t-Bu 2 -4-Me-OC 6 H 2 ) was prepared by treating the bromo precursor 1 with NaOAr, whereas the analogous reaction with NaOEt gave instead the protonated or ethoxy-functionalized ligand NC(H)N pz (major) and NC(OEt)N pz (minor). The new complexes 1−3 were fully characterized, including solid-state structures. Attempted oxidation of these complexes failed to give the target trivalent derivatives, leading instead to intractable, deeply colored Ni-containing solids, various ligand-derived side products, or an unusual I 2 adduct. For example, treatment of 1 or 2 with N-bromosuccinimide gave sparingly soluble dark solids that appear to be paramagnetic, whereas 3 reacted with Br 2 to give short-lived dark intermediates that decomposed over seconds to give ArOH. Reaction of the bromo complexes with aqueous H 2 O 2 (30%) gave the functionalized ligands Br-NC(OH)N pz and NC(OH)N pz (from 1) or MeO-NC(OH)N pz (from 2), whereas 1 reacted with I 2 to generate (NCN pz )NiBr•I 2 , an iodine adduct displaying weak Br−I interactions. Heating 1 in EtOH in air generated NC(OEt)N pz . This ligand derivatization could be extended to other alcohols (MeOH, i-PrOH, CF 3 CH 2 OH) and amines (morpholine, cyclohexylamine, aniline). Possible mechanistic scenarios for the observed oxidative, Ni-promoted C ipso −X bond formation reactions are discussed in the context of relevant literature precedents.