sodium acetate; 3-chloro-benzenecarboperoxoic acid in dichloromethane T=20°C; 6 h;

1.1: diisopropylamine / Pd(PPh3)4 / tetrahydrofuran / 0.33 h / 20 °C 1.2: 99 percent / CuI / tetrahydrofuran / 12 h 2.1: 99 percent / LAH / tetrahydrofuran / 20 h / Heating 3.1: 95 percent / imidazole / dimethylformamide / 0 - 20 °C 4.1: 72 percent / m-CPBA; NaOAc / CH2Cl2 / 6 h / 20 °C View Scheme

1.1: diisopropylamine / Pd(PPh3)4 / tetrahydrofuran / 0.33 h / 20 °C 1.2: 99 percent / CuI / tetrahydrofuran / 12 h 2.1: 99 percent / LAH / tetrahydrofuran / 20 h / Heating 3.1: 95 percent / imidazole / dimethylformamide / 0 - 20 °C 4.1: 72 percent / m-CPBA; NaOAc / CH2Cl2 / 6 h / 20 °C View Scheme

1: 95 percent / imidazole / dimethylformamide / 0 - 20 °C 2: 72 percent / m-CPBA; NaOAc / CH2Cl2 / 6 h / 20 °C View Scheme

1: 99 percent / LAH / tetrahydrofuran / 20 h / Heating 2: 95 percent / imidazole / dimethylformamide / 0 - 20 °C 3: 72 percent / m-CPBA; NaOAc / CH2Cl2 / 6 h / 20 °C View Scheme

1.1: 79.7 percent / copper(I) iodide / tetrahydrofuran / -40 - 20 °C 2.1: 46.7 percent / MgBr2 / diethyl ether / 20 °C 3.1: 66.4 percent / anhydrous K2CO3 / dimethylformamide / 36 h / 20 °C 4.1: 97 percent / PPTS / CH2Cl2 / 7 h / 20 °C 5.1: Grubbs' second generation metathesis catalyst / CH2Cl2 / 0.5 h / Heating 5.2: ethyl vinyl ether / CH2Cl2 / 0.25 h 5.3: 21 mg / N-methylquinolinium hexafluorophosphate; sodium acetate; anhydrous sodium thiosulfate / O2 / 1,2-dichloro-ethane; toluene / 5 h / 20 °C / Irradiation View Scheme