Me2Cu(CN)Li2 in tetrahydrofuran; water; acetic acid

pyridine hydrogenfluoride in acetonitrile 2 h; Ambient temperature;

1: 51 percent / sodium nitrite, phloroglucinol / dimethylsulfoxide / 20 h / Ambient temperature 2: 1) 3N sodium hydroxide; 3) acetic acid / 1) H2O, 0 deg C, 3 h; 2) H2O, 0 deg C, 5 h; 3) H2O, room temp., 20 h 3: 79 percent / mesyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C 4: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 5: 42 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 0.17 h / 110 °C 6: 88 percent / hydrogen fluoride-pyridine / acetonitrile / 2 h / Ambient temperature View Scheme

1: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 2: 42 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 0.17 h / 110 °C 3: 88 percent / hydrogen fluoride-pyridine / acetonitrile / 2 h / Ambient temperature View Scheme

1: 1) 3N sodium hydroxide; 3) acetic acid / 1) H2O, 0 deg C, 3 h; 2) H2O, 0 deg C, 5 h; 3) H2O, room temp., 20 h 2: 79 percent / mesyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C 3: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 4: 42 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 0.17 h / 110 °C 5: 88 percent / hydrogen fluoride-pyridine / acetonitrile / 2 h / Ambient temperature View Scheme

1: 79 percent / mesyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C 2: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 3: 42 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 0.17 h / 110 °C 4: 88 percent / hydrogen fluoride-pyridine / acetonitrile / 2 h / Ambient temperature View Scheme

1: 42 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 0.17 h / 110 °C 2: 88 percent / hydrogen fluoride-pyridine / acetonitrile / 2 h / Ambient temperature View Scheme

1: (i) iBu2AlH, (ii) I2, THF View Scheme

Multistep reaction;

Multistep reaction;