trimethylsilyl bromide; tetrabutylammomium bromide; cobalt(II) dibromide; 4 A molecular sieve in dichloromethane T=25°C;

1: N,N-dicyclohexylcarbodiimide; trifluoroacetic acid; pyridine / dimethylsulfoxide; benzene / 24 h / 20 °C 2: Et3N; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 3 h / Heating 3: PdCl2 / dioxane; H2O / 3 h / 60 °C 4: 89.5 percent / NaBH4 / methanol / 0.5 h / -78 °C 5: NaOH / methanol / 12 h / 20 °C 6: 14.8 mg / H2 / Pd(OH)2/C / methanol / 24 h / 20 °C View Scheme

Fe(ClO4)3*6H2O in acetonitrile T=80°C; 5 h;

1: N,N-dicyclohexylcarbodiimide; trifluoroacetic acid; pyridine / dimethylsulfoxide; benzene / 24 h / 20 °C 2: Et3N; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 3 h / Heating 3: PdCl2 / dioxane; H2O / 3 h / 60 °C 4: 96.3 percent / NaBH4 / methanol / 0.5 h / 0 °C 5: NaOH / methanol / 12 h / 20 °C 6: 12.4 mg / H2 / Pd(OH)2/C / methanol / 24 h / 20 °C View Scheme

View Scheme