We investigated the optimal conditions for the cascade 1,2-N-shift/C-H coupling of methyl 3-bromo-2-(dibenzylamino) propanoate 1a as the model feedstock (Table ). After extensive investigation of the reaction parameters (see SI for details), we found that the C-H coupling product (2aa) was obtained in 75% yield when NiBr2(dme) (10 mol%), pyridine-imidazoline L1 (12 mol%), and B2neo2 (1.5 equiv.) were used as the catalyst, ligand, and reductant, respectively, in the presence of K2CO3. In contrast, almost no regioselective isomer 2a′ formed via the direct C-H coupling of the pre-halogenated sites was detected using GC-MS. It is to Table . Optimization of Reaction Conditions for 3aa. a