triethylamine; palladium diacetate; 2-dicyclohexylphosphino-1,1'-biphenyl in 1,4-dioxane T=80°C;

1: Me2PhSiBpin With potassium methanolate in ethylene glycol dimethyl ether T=30°C; 0.166667 h; Inert atmosphere; 2: 1-methyl-5-bromoindole in ethylene glycol dimethyl ether T=30°C; 1 h;

palladium diacetate; triethylamine in 1,4-dioxane under Ar atm.; Schlenk flask charged with Pd(CH3COO)2 and P(C6H11)2(C6H4C6H5); evapd.; filled (Ar); 1,4-dioxane added; stirred for 30 min at room temp.; Et3N added; soln. of bromoindole in dioxane added; neat pinacolborane added; stirred at 80°C; cooled to room temp.; Celite and activated charcoal added; stirred for 15 min; filtered; solvent removed (vac.); residue diluted (cyclohexane); filtered through a short pad of neutral alumina; purified by column chromy (SiO2, cyclohexane/ethyl acetate);

in diethyl ether T=20°C;

1.1: NaH / 1,2-dimethoxy-ethane; dimethylsulfoxide / 0.5 h / 20 °C 1.2: 75 percent / 1,2-dimethoxy-ethane; dimethylsulfoxide / 20 °C 2.1: 78 percent / Et3N / Pd(OAc)2; (2-Ph-C6H4)-P(C6H11)2 / dioxane / 80 °C View Scheme

1.1: palladium diacetate; potassium iodide; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl; triethylamine / ethyl acetate / 16 h / 50 °C / |Inert atmosphere; |Schlenk technique 2.1: methanol / ethyl acetate / 1 h / -5 - 20 °C / |Inert atmosphere; |Schlenk technique 2.2: 4 h / 20 °C / |Inert atmosphere; |Schlenk technique View Scheme