pyridine; pyridine hydrogenfluoride in acetonitrile 4 h; Ambient temperature;

1: conc. H2SO4 / 10 h / Ambient temperature 2: 1.) (c-C6H11)2BH, 2.) aq. NaOH / 2.) Pd(PPh3)4 / 1.) THF, r.t., 1 h, 2.) benzene, 65 deg C, 1 h 3: 70percent m-CPBA / CH2Cl2 / 1 h / Ambient temperature 4: BF3*Et2O, MeOH / 0.5 h / 0 °C 5: 1.) t-BuLi, 2-thienyl(cyano)copper lithium / 1.) pentane, Et2O, -78 deg C, 30 min; THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h 6: 93 percent / HF*pyridine, pyridine / acetonitrile / 4 h / Ambient temperature View Scheme

1: 89 percent / NaBr, BF3*Et2O / acetone / 0.5 h / Ambient temperature 2: 1.) (c-C6H11)2BH, 2.) aq. NaOH / 2.) Pd(PPh3)4 / 1.) THF, r.t., 1 h, 2.) benzene, 65 deg C, 1 h 3: 70percent m-CPBA / CH2Cl2 / 1 h / Ambient temperature 4: BF3*Et2O, MeOH / 0.5 h / 0 °C 5: 1.) t-BuLi, 2-thienyl(cyano)copper lithium / 1.) pentane, Et2O, -78 deg C, 30 min; THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h 6: 93 percent / HF*pyridine, pyridine / acetonitrile / 4 h / Ambient temperature View Scheme

1: 1.) (c-C6H11)2BH, 2.) aq. NaOH / 2.) Pd(PPh3)4 / 1.) THF, r.t., 1 h, 2.) benzene, 65 deg C, 1 h 2: 70percent m-CPBA / CH2Cl2 / 1 h / Ambient temperature 3: BF3*Et2O, MeOH / 0.5 h / 0 °C 4: 1.) t-BuLi, 2-thienyl(cyano)copper lithium / 1.) pentane, Et2O, -78 deg C, 30 min; THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h 5: 93 percent / HF*pyridine, pyridine / acetonitrile / 4 h / Ambient temperature View Scheme

1: 1.) (c-C6H11)2BH, 2.) aq. NaOH / 2.) Pd(PPh3)4 / 1.) THF, r.t., 1 h, 2.) benzene, 65 deg C, 1 h 2: 70percent m-CPBA / CH2Cl2 / 1 h / Ambient temperature 3: BF3*Et2O, MeOH / 0.5 h / 0 °C 4: 1.) t-BuLi, 2-thienyl(cyano)copper lithium / 1.) pentane, Et2O, -78 deg C, 30 min; THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h 5: 93 percent / HF*pyridine, pyridine / acetonitrile / 4 h / Ambient temperature View Scheme

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-BuLi; 2) CuI, Bu3P; 5) 25percent aq. TiCl3, NH4OAc 5: 87 percent / hydrogen fluoride-pyridine / acetonitrile / 2.5 h / Ambient temperature View Scheme

1: 1) t-BuLi; 2) CuI, Bu3P; 5) 25percent aq. TiCl3, NH4OAc 2: 87 percent / hydrogen fluoride-pyridine / acetonitrile / 2.5 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-BuLi; 2) CuI, Bu3P; 5) 25percent aq. TiCl3, NH4OAc 4: 87 percent / hydrogen fluoride-pyridine / acetonitrile / 2.5 h / Ambient temperature View Scheme

1: 79 percent / mesyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C 2: 1) t-BuLi; 2) CuI, Bu3P; 5) 25percent aq. TiCl3, NH4OAc 3: 87 percent / hydrogen fluoride-pyridine / acetonitrile / 2.5 h / Ambient temperature View Scheme

1: 1.) t-BuLi, 2-thienyl(cyano)copper lithium / 1.) pentane, Et2O, -78 deg C, 30 min; THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h 2: 93 percent / HF*pyridine, pyridine / acetonitrile / 4 h / Ambient temperature View Scheme