sodium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-benzyl-N,N,N-triethylammonium chloride in benzene T=5°C; 3 h;

1: NaBH4 / methanol / 0.5 h / 0 °C 2: HgO, I2 / benzene / 1 h 3: PCC / CH2Cl2 4: 99 percent / acetonitrile / 3 h / Irradiation 5: 91 percent / NaBH4 / methanol; dioxane / 1 h / 0 °C 6: 95 percent / benzyltriethylammonium chloride, CuI, Pd<P(Ph)3>4, 2.5 N aq. NaOH / benzene / 3 h / 5 °C View Scheme

1: 99 percent / acetonitrile / 3 h / Irradiation 2: 91 percent / NaBH4 / methanol; dioxane / 1 h / 0 °C 3: 95 percent / benzyltriethylammonium chloride, CuI, Pd<P(Ph)3>4, 2.5 N aq. NaOH / benzene / 3 h / 5 °C View Scheme

1: HgO, I2 / benzene / 1 h 2: PCC / CH2Cl2 3: 99 percent / acetonitrile / 3 h / Irradiation 4: 91 percent / NaBH4 / methanol; dioxane / 1 h / 0 °C 5: 95 percent / benzyltriethylammonium chloride, CuI, Pd<P(Ph)3>4, 2.5 N aq. NaOH / benzene / 3 h / 5 °C View Scheme

1: PCC / CH2Cl2 2: 99 percent / acetonitrile / 3 h / Irradiation 3: 91 percent / NaBH4 / methanol; dioxane / 1 h / 0 °C 4: 95 percent / benzyltriethylammonium chloride, CuI, Pd<P(Ph)3>4, 2.5 N aq. NaOH / benzene / 3 h / 5 °C View Scheme

1: 91 percent / NaBH4 / methanol; dioxane / 1 h / 0 °C 2: 95 percent / benzyltriethylammonium chloride, CuI, Pd<P(Ph)3>4, 2.5 N aq. NaOH / benzene / 3 h / 5 °C View Scheme