Evaluation of reaction conditions for the nickel-catalyzed Suzuki–Miyaura coupling / transfer hydrogenation cascade of amide 1 with phenyl boronates and reductants. Standard conditions unless otherwise noted: amide substrate (0.20 mmol, 1.0 equiv); phenyl boronate (0.50–0.80 mmol, 2.5–4.0 equiv); reductant (0.50 equiv, 2.5 equiv); K3PO4 (0.80 mmol, 4.0 equiv); H2O (0.40 mmol, 2.0 equiv); Ni(cod)2 (0.010–0.020 mmol, 5–10 mol%); 2 (0.020–0.040 mmol, 10–20 mol%); solvent (1.0 M); 120 °C; 16 h in a sealed vial. [a] Yield determined by 1H NMR analysis using 1,3,5-trimethoxybenzene as an external standard.