1,1'-bis-(diphenylphosphino)ferrocene; triethylamine; palladium diacetate in N,N-dimethyl-formamide T=20°C; 18 h;

1.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 3 h / -78 °C 1.2: 90 percent / tetrahydrofuran / -78 - 20 °C 2.1: 65 percent / 1,1'-bis(diphenylphosphino)ferrocene; Et3N / Pd(OAc)2 / dimethylformamide / 18 h / 20 °C View Scheme

T=420°C;

1: 95 percent / potassium carbonate / toluene / 24 h / Heating 2: 60 percent / lithium aluminum hydride / toluene / 0 °C 3: 87 percent / 2 h / 160 °C 4: 71 percent / potassium hydroxide; hydrazine hydrate / ethane-1,2-diol / 3 h / Heating 5: 81 percent / sodium cyanoborohydride / H2O; acetonitrile / 0.17 h / 20 °C View Scheme

1: 95 percent / potassium carbonate / toluene / 24 h / Heating 2: 60 percent / lithium aluminum hydride / toluene / 0 °C 3: 87 percent / 2 h / 160 °C 4: 71 percent / potassium hydroxide; hydrazine hydrate / ethane-1,2-diol / 3 h / Heating View Scheme

1: 95 percent / potassium carbonate / toluene / 24 h / Heating 2: 60 percent / lithium aluminum hydride / toluene / 0 °C 3: 80 percent / 2 h / 160 °C 4: 70 percent / potassium hydroxide; hydrazine hydrate / ethane-1,2-diol / 3 h / Heating View Scheme