potassium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethanol; toluene T=100°C; Suzuki cross-coupling; 5 h;

1: With potassium acetate in water; toluene T=90°C; 12 h; 2: With sodium hydroxide in water; toluene T=50 - 70°C; 5 h;

1: palladium(II) dichloride bis[bis(diphenylphosphine)ferrocene]; potassium phosphate / N,N-dimethyl-formamide / 80 °C / |Inert atmosphere 2: sodium tetrahydroborate / methanol / 0.5 h / 0 °C 3: MMPP / methanol / 0.5 h / 0 - 20 °C View Scheme

1: 4-(dimethylamino)picolinaldehyde N,N-dibenzylhydrazone; bis(η4-1,5-cyclooctadiene)-di-μ-methoxy-diiridium(I) / tetrahydrofuran / 24 h / 80 °C / |Inert atmosphere 2: palladium(II) dichloride bis[bis(diphenylphosphine)ferrocene]; potassium phosphate / N,N-dimethyl-formamide / 80 °C / |Inert atmosphere 3: sodium tetrahydroborate / methanol / 0.5 h / 0 °C 4: MMPP / methanol / 0.5 h / 0 - 20 °C View Scheme

1: With triethylaluminum in toluene T=0°C; 0.0833333 h; 2: With diisobutylaluminium azide in toluene T=100°C;

dimethyl sulfoxide; triethylamine in hexane; dichloromethane