However, substrates with ortho substituents (2ae-2ag) showed decreased yields due to unreacted starting material. Benzo[d] [1,3]dioxol-5-amine could also undergo the sequential process to give 2ah in 61% yield. The reaction also proceeded smoothly with more complex substrates bearing drug moieties to deliver analogues of Butamben (2ai), Menthol (2aj), and Tocopherol (2ak). Finally, we investigated the reaction with internal alkene containing substrates. In these cases, the starting material was not completely consumed, likely due to the slower rate of HAT from the metal catalyst. However, low product yields of 2al and 2am were nevertheless isolated.