Scheme 1. Substrate scope. (A) Using six-membered bromoarenes. (B) Using bromoheteroles. (C) Using N-tosylhydrazones. aConditions. 1 or 5 (0.20 mmol), 2 (0.20 mmol), 3 (0.20 mmol), Pd(OAc)2 (5.0 mol%), L1 (20 mol%), NaH (1.0 equiv.), 3 Å MS (50 mg), toluene (1.0 mL), 60 °C, 12 h. NMR yields were shown and numbers in parenthesis are isolated yield. bDPEphos was used instead of L1. c2.0 equiv. of 2, 3, and NaH. Cyclohexane as solvent. d1.5 equiv. of 3 and NaH. e90 °C. fPd(cod)Cl2 (5.0 mol%), DPEphos (10 mol%) as catalyst and KBr (2.0 equiv.) were used. g40 °C. h50 °C. i70 °C. jDPEphos at 80 °C. kCyclohexane as solvent. lConditions. 1A or 5A (0.20 mmol), 7 (0.30 mmol), 3a (0.30 mmol), Pd(OAc)2 (5.0 mol%), L1 (20 mol%), NaH (3.0 equiv.), 3 Å MS (50 mg), 1,4-dioxane (1.0 mL), 50 °C, 36 h.
