1: With boron tribromide in dichloromethane T=20°C; Inert atmosphere; 2: With water in dichloromethane 0.0833333 h;

hydrogen; Wilkinson's catalyst in ethanol

sodium tetrahydroborate; nickel dichloride

1: 100 percent / aq. H2SO4 / Heating 2: 100 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C 3: 86 percent / PdCl2(dppf); dppf; AcOK / dioxane / 80 °C 4: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 5: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 6: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 7: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 8: 52 percent / CuI / tetrahydrofuran / -26 °C 9: 89 percent / aq. HCl / methanol / 44 h / 20 °C 10: 18 percent / H2 / Wilkinson's catalyst / ethanol View Scheme

1: 98 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C 2: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C 3: 100 percent / imidazole / dimethylformamide / 20 °C 4: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 5: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 6: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 7: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 8: 52 percent / CuI / tetrahydrofuran / -26 °C 9: 89 percent / aq. HCl / methanol / 44 h / 20 °C 10: 18 percent / H2 / Wilkinson's catalyst / ethanol View Scheme

1: 100 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C 2: 86 percent / PdCl2(dppf); dppf; AcOK / dioxane / 80 °C 3: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 4: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 5: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 6: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 7: 52 percent / CuI / tetrahydrofuran / -26 °C 8: 89 percent / aq. HCl / methanol / 44 h / 20 °C 9: 18 percent / H2 / Wilkinson's catalyst / ethanol View Scheme

1: 80 percent / HBF4; N-bromosuccinimide / acetonitrile / -20 - 20 °C 2: 98 percent / i-Pr2NEt / dimethylformamide / 3 h / 20 °C 3: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C 4: 100 percent / imidazole / dimethylformamide / 20 °C 5: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 6: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 7: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 8: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 9: 52 percent / CuI / tetrahydrofuran / -26 °C 10: 89 percent / aq. HCl / methanol / 44 h / 20 °C 11: 18 percent / H2 / Wilkinson's catalyst / ethanol View Scheme

1: 100 percent / imidazole / dimethylformamide / 20 °C 2: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 3: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 4: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 5: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 6: 52 percent / CuI / tetrahydrofuran / -26 °C 7: 89 percent / aq. HCl / methanol / 44 h / 20 °C 8: 18 percent / H2 / Wilkinson's catalyst / ethanol View Scheme

1: 86 percent / PdCl2(dppf); dppf; AcOK / dioxane / 80 °C 2: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 3: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 4: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 5: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 6: 52 percent / CuI / tetrahydrofuran / -26 °C 7: 89 percent / aq. HCl / methanol / 44 h / 20 °C 8: 18 percent / H2 / Wilkinson's catalyst / ethanol View Scheme

1: 100 percent / DIBAL-H / CH2Cl2 / 2 h / -78 °C 2: 100 percent / imidazole / dimethylformamide / 20 °C 3: 87 percent / PdCl2(dppf); dppf; K3PO4 / dioxane / 108 °C 4: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 5: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 6: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 7: 52 percent / CuI / tetrahydrofuran / -26 °C 8: 89 percent / aq. HCl / methanol / 44 h / 20 °C 9: 18 percent / H2 / Wilkinson's catalyst / ethanol View Scheme