potassium phosphate; CM-phos; palladium diacetate; triethylamine in tert-butyl alcohol T=50°C; Suzuki coupling; 24 h; Inert atmosphere;

1: 78 percent / HMPA; KHMDS / tetrahydrofuran; toluene / 2 h / -78 °C 2: 69 percent / TMEDA / Pd(PPh3)2Cl2 / tetrahydrofuran / 1 h / 40 °C View Scheme

1.1: 74 percent / ethanol / 3.5 h / 20 °C 2.1: TMEDA; n-butyllithium / hexane / 1.75 h / -78 - 18 °C 2.2: 5 percent / hexane / 0 - 18 °C 3.1: 1-chloroethyl chloroformate / CH2Cl2 / 2 h / Heating 3.2: MeOH / 1 h / Heating 3.3: 80 percent / aq. KOH / methanol; dioxane / 16 h / 18 °C 4.1: 99 percent / TBAF / Pd2(dba)3*CHCl3 / tetrahydrofuran / 19 h / 20 °C View Scheme

1.1: TMEDA; n-butyllithium / hexane / 1.75 h / -78 - 18 °C 1.2: 5 percent / hexane / 0 - 18 °C 2.1: 1-chloroethyl chloroformate / CH2Cl2 / 2 h / Heating 2.2: MeOH / 1 h / Heating 2.3: 80 percent / aq. KOH / methanol; dioxane / 16 h / 18 °C 3.1: 99 percent / TBAF / Pd2(dba)3*CHCl3 / tetrahydrofuran / 19 h / 20 °C View Scheme

1.1: 1-chloroethyl chloroformate / CH2Cl2 / 2 h / Heating 1.2: MeOH / 1 h / Heating 1.3: 80 percent / aq. KOH / methanol; dioxane / 16 h / 18 °C 2.1: 99 percent / TBAF / Pd2(dba)3*CHCl3 / tetrahydrofuran / 19 h / 20 °C View Scheme

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate in water; N,N-dimethyl-formamide T=80°C; Suzuki coupling;

acid Heating;

palladium diacetate

1: palladium on activated charcoal; hydrogen / methanol / 15 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 5 h / 0 - 20 °C 3: sodium iodide; sodium carbonate / N,N-dimethyl-formamide / 4 h / 80 °C 4: hydrazine hydrate / ethanol / 2 h / 70 °C View Scheme