A broad scope of amine coupling partners has also been developed. A proline derivative was successfully converted to the corresponding acylated product 3p in 77% yield. Different protecting groups were well tolerated, including CBz, Ac, and Bz (3q-r). Piperidine, one of the most prevalent motifs of pharmaceutical ingredient cores, was successfully applied to the dehydrogenative coupling, together with a regioselective C-H functionalization using Boc-morpholine to afford products 3t and 3u. Orthogonal functionalization of multiple heteroatoms of similar reactivity has been long sought after in organic synthesis, 3c and we took advantage of Ts as a deactivating group to enable a regioselective activation of the C-H bond proximal to the Boc-protected nitrogen of piperazine (3v). Such substrate-controlled regioselectivity has also been observed by Nicewicz and co-workers. The desired acylation was also observed in acyclic systems, with simple building blocks including carbamate and urea derivatives of dimethylamine (3w and 3x).