N-Alkylation of isatins can be achieved utilizing trichloroacetimidate electrophiles and a Lewis acid catalyst. These reactions provide access to N-alkyl isatins, versatile scaffolds which are often employed in the synthesis of pharmaceutical lead structures as well as natural products. Secondary trichloroacetimidates that are precursors to stabilized carbocations provided excellent yields of the isatin product. Substitution was well tolerated on the isatin, although reduced reactivity was observed with C7-substitution, likely due to the steric effects. Solvent effects can be used to favor O-alkylation under similar reaction conditions.