thionyl chloride in 1,4-dioxane 0.5 h; Heating;

1: 98 percent / sodium phosphate monobasic dihydrate, 35 percent hydrogen peroxide, sodium chlorite / acetonitrile; H2O / 5 h / 10 °C 2: oxalyl chloride / dimethylformamide; CH2Cl2 / 1.5 h / Heating View Scheme

1: phenyliodine(III)diacetate (PIDA); I2; H2SO4 / acetic acid; acetic anhydride / 20 °C 2: SOCl2 / toluene / Heating View Scheme

1.2: potassium iodide 2.1: PCl5 / Heating View Scheme

1.1: 0.5 h / Inert atmosphere 2.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; zinc(II) chloride; zinc / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere 3.1: potassium hydroxide / aacetone / 2 h / Reflux; Inert atmosphere 4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 2 h / Inert atmosphere; Reflux 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere 5.2: 20 °C View Scheme

0.5 h; Inert atmosphere;

1.1: triethylamine / dichloromethane / 0.08 h / 0 °C / |Inert atmosphere 1.2: 0 - 20 °C / |Inert atmosphere 2.1: 1,10-phenanthroline; potassium tert-butylate / 1,3,5-trimethyl-benzene / 6 h / 100 °C / |Inert atmosphere View Scheme

1: 1.44 g / Et3N / CH2Cl2 / 16 h / Heating 2: 35 percent / Pd(OAc)2; P(o-tolyl)3; Ag2CO3 / dimethylformamide / 0.5 h / Heating 3: 95 percent / formic acid; AcOH / Pd black / 1.5 h / 20 °C View Scheme

1: 2.08 g / NEt3 / CH2Cl2 / 1 h / Ambient temperature 2: 96.4 percent / NaH / dimethylformamide / 0.5 h / Ambient temperature 3: 89 percent / tris(2-methylphenyl)phosphine, silver carbonate / Pd(OAc)2 / dimethylformamide / 2 h / Heating View Scheme