Scheme 4.

Coupling with bulky (hetero)aryl halides^a

^a Conditions: (Het)ArX (1 mmol), NH₃ (3 mmol), NaO^tBu (1.4 mmol), 3b (2 mol %), L7 (2 mol %), dioxane (10 mL, 0.10 M), 24 h; isolated products, average of two runs; ratios of arylamine to diarylamine (1°:2°) determined by ¹H NMR. ^b Conditions: (Het)ArX (0.25 mmol), NH₃ (0.75 mmol), NaO^tBu (0.35 mmol), Pd₂dba₃ (1 mol %), L6/L7 (4 mol %), dioxane (2.5 mL, 0.10 M), 100 °C, 24 h; ¹H NMR yield of crude product. ^c 3b and L7 (5 mol %), dioxane (0.143 M).