N-benzyl-trimethylammonium hydroxide T=20°C; Condensation; 3 h;

tris(dimethylamino)-sulphonium difluorotrimethylsilicate in N,N-dimethyl-formamide T=15°C; 2.5 h;

1.1: 90 percent / MoO5*HMPA / 168000 h / 20 °C 2.1: 50 percent / 10-camphorsulfonic acid / acetonitrile / 0.5 h / Heating 3.1: Br2 / CH2Cl2 / 2 h / 0 °C 4.1: molecular sieves 4 Angstroem / dimethylformamide / 48 h / 20 °C 5.1: DBU / toluene / 3 h / 40 °C 5.2: LiOH / methanol / 72 h / 20 °C 6.1: 2,6-lutidine / CH2Cl2 / 72 h / 20 °C 6.2: 69 percent / AcOH / H2O; tetrahydrofuran / 2 h / 80 °C 7.1: 12 percent / O2; PdCl2; CuCl / H2O; dioxane / 24 h / 50 °C 8.1: 75 percent / tris(dimethylamino)sulfur (trymethylsilyl)difluoride / dimethylformamide / 2.5 h / 15 °C View Scheme

1: 82 percent / p-TSA / cyclohexane / Heating 2: 69 percent / H2 / 10 percent Pd/C / methanol 3: 78 percent / Br2 / ethanol; CHCl3 / 3 h 4: tert-butyl nitrite / dimethylformamide / 10 h / 60 °C 5: oxalic acid / 60 °C 6: 96 percent / benzyltrimethylammonium hydroxide / 3 h / 20 °C View Scheme

1: 70 percent / KNO3; H2SO4 / 1 h / 0 °C 2: 82 percent / p-TSA / cyclohexane / Heating 3: 69 percent / H2 / 10 percent Pd/C / methanol 4: 78 percent / Br2 / ethanol; CHCl3 / 3 h 5: tert-butyl nitrite / dimethylformamide / 10 h / 60 °C 6: oxalic acid / 60 °C 7: 96 percent / benzyltrimethylammonium hydroxide / 3 h / 20 °C View Scheme

1.1: 2,6-lutidine / CH2Cl2 / 72 h / 20 °C 1.2: 69 percent / AcOH / H2O; tetrahydrofuran / 2 h / 80 °C 2.1: 12 percent / O2; PdCl2; CuCl / H2O; dioxane / 24 h / 50 °C 3.1: 75 percent / tris(dimethylamino)sulfur (trymethylsilyl)difluoride / dimethylformamide / 2.5 h / 15 °C View Scheme

1: 12 percent / O2; PdCl2; CuCl / H2O; dioxane / 24 h / 50 °C 2: 75 percent / tris(dimethylamino)sulfur (trymethylsilyl)difluoride / dimethylformamide / 2.5 h / 15 °C View Scheme

1: 78 percent / Br2 / ethanol; CHCl3 / 3 h 2: tert-butyl nitrite / dimethylformamide / 10 h / 60 °C 3: oxalic acid / 60 °C 4: 96 percent / benzyltrimethylammonium hydroxide / 3 h / 20 °C View Scheme

1: tert-butyl nitrite / dimethylformamide / 10 h / 60 °C 2: oxalic acid / 60 °C 3: 96 percent / benzyltrimethylammonium hydroxide / 3 h / 20 °C View Scheme

1: 85 percent / H2SO4 (86 percent) / 0.01 h / microwave irradiation 2: 96 percent / aq. BnMe3NOH / 3 h / 20 °C View Scheme