lithium chloride; copper dichloride in tetrahydrofuran T=-5 - 20°C; 24 h;

potassium carbonate in tetrahydrofuran 12 h; Reflux;

lithium chloride; copper dichloride in tetrahydrofuran T=-5 - 20°C; 5 h;

1.1: 40 percent / 8 h / 80 °C 2.1: PPh3; CCl4 / acetonitrile / 3 h / 50 °C 2.2: 60 percent / acetonitrile / 6 h / 50 °C 3.1: 32 percent / Cs2CO3 / CH2Cl2 / 72 h / 25 °C 4.1: 89 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 5.1: 68 percent / imidazole; PPh3; I2 / diethyl ether; acetonitrile / 24 h / 25 °C 6.1: 67 percent / LiCl; CuCl2 / tetrahydrofuran / 24 h / -5 - 20 °C View Scheme

1.1: PPh3; CCl4 / acetonitrile / 3 h / 50 °C 1.2: 60 percent / acetonitrile / 6 h / 50 °C 2.1: 32 percent / Cs2CO3 / CH2Cl2 / 72 h / 25 °C 3.1: 89 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 4.1: 68 percent / imidazole; PPh3; I2 / diethyl ether; acetonitrile / 24 h / 25 °C 5.1: 67 percent / LiCl; CuCl2 / tetrahydrofuran / 24 h / -5 - 20 °C View Scheme

1: 93 percent / pyridine / CH2Cl2 / 24 h / -5 - 25 °C 2: 98 percent / Et3N; SOCl2 / CH2Cl2 / 5 h / 0 - 25 °C 3: 32 percent / Cs2CO3 / CH2Cl2 / 72 h / 25 °C 4: 89 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 5: 68 percent / imidazole; PPh3; I2 / diethyl ether; acetonitrile / 24 h / 25 °C 6: 67 percent / LiCl; CuCl2 / tetrahydrofuran / 24 h / -5 - 20 °C View Scheme

1: 68 percent / imidazole; PPh3; I2 / diethyl ether; acetonitrile / 24 h / 25 °C 2: 67 percent / LiCl; CuCl2 / tetrahydrofuran / 24 h / -5 - 20 °C View Scheme

1: 89 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 2: 68 percent / imidazole; PPh3; I2 / diethyl ether; acetonitrile / 24 h / 25 °C 3: 67 percent / LiCl; CuCl2 / tetrahydrofuran / 24 h / -5 - 20 °C View Scheme

1: 32 percent / Cs2CO3 / CH2Cl2 / 72 h / 25 °C 2: 89 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 3: 68 percent / imidazole; PPh3; I2 / diethyl ether; acetonitrile / 24 h / 25 °C 4: 67 percent / LiCl; CuCl2 / tetrahydrofuran / 24 h / -5 - 20 °C View Scheme

1: 98 percent / Et3N; SOCl2 / CH2Cl2 / 5 h / 0 - 25 °C 2: 32 percent / Cs2CO3 / CH2Cl2 / 72 h / 25 °C 3: 89 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating 4: 68 percent / imidazole; PPh3; I2 / diethyl ether; acetonitrile / 24 h / 25 °C 5: 67 percent / LiCl; CuCl2 / tetrahydrofuran / 24 h / -5 - 20 °C View Scheme