Reactions of the well-defined two-coordinate indium "carbene analogue" [In{N(Dipp)-C(Me)}(2)CH] (Dipp = 2,6-(Pr2C6H3)-Pr-i) have been studied. Reactions of MeI, (PrI)-Pr-i, and (BuI)-Bu-t with [In{N(Dipp)C(Me)}(2)CH] formed by the in situ reaction of InI, [K{N(SiMe3)(2)}], and the iminoenamine ligand precursor successfully yielded the oxidative addition products [InRI{N(Dipp)C(Me)}(2)CH] (R = Me, Pr-i, Bu-t). The results of NMR investigations, which indicated the formation of a series of four-coordinate indium(III) complexes in C6D6 solution, were confirmed in the solid-state by single-crystal X-ray diffraction. Similar reactions employing alkyl bromides were unsuccessful and resulted in the isolation of the corresponding iodides, apparently by metathesis of the bromide oxidative addition product with KI formed during the initial InI metathesis. Reactions of isolated samples of [In{N(Dipp)C(Me)}(2)CH] with (PrBr)-Pr-i and (BuBr)-Bu-t, however, were straightforward and resulted in the successful isolation of the analogous iso-propyl and tert-butyl indium(III) bromide complexes. These were also fully characterized by H-1 and C-13 NMR and single-crystal X-ray diffraction experiments. In contrast, no reaction was observed between [In{N(Dipp)-C(Me)}(2)CH] and aryl halides or alkyl chlorides.