The Chan-Evans-Lam reaction allows for the copper-promoted oxidative coupling of carbon to nitrogen. Although the reaction has been established for the coupling of sp2-hybridized carbon to nitrogen, the reaction remains underdeveloped for the coupling of sp3-hybridized carbon to nitrogen. There is wide reaching potential of the Chan-Evans-Lam alkyl-amination reaction within the synthetic community. The focus of this research is to investigate the alkylation of aryl amines and probe the viability of functionality on aryl amines. It has been discovered that the alkylation of aryl amines can be achieved in moderate yields, 60-72%. An optimization has been demonstrated by coupling aniline to potassium octyltrifluoroborate in the presence of copper (II) acetate monohydrate and cesium carbonate in tert-butanol. By-product formation can be minimized by substitution of atmospheric O2 oxidant for di-tert-butyl peroxide as an oxidant under an atmosphere of N2. Furthermore, addition of 4 Å molecular sieves is required to achieve high yields. This reaction requires temperatures of 90 ̊C. Application of optimized yields to aniline analogues containing p-substituted functionality was subsequently probed to show compatibility.