sulfuric acid; iodine; periodic acid; H-β zeolite in water; acetic acid T=20 - 118°C; 6 h; Heating / reflux; Product distribution / selectivity;

1: With hydrogenchloride; sodium nitrite in water T=0°C; 2.5 h; 2: With potassium iodide in water T=80°C; 14 h; Cooling with ice;

[bis(acetoxy)iodo]benzene; iodine; palladium diacetate; tetra-(n-butyl)ammonium iodide in 1,2-dichloro-ethane T=80°C; 2 h;

potassium iodide; sodium nitrite in 3-N hydrochloric acid; water

(i) H2, aq. NaOH, Pd-CaCO3, (ii) NaNO2, aq. HCl, (iii) KI, aq. HCl; Multistep reaction;

1: sulfuric acid / methanol / 18 h / 65 °C / |Large scale 2: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / 2-methyl tetrahydrofuran / 1 h / 60 - 77 °C / |Inert atmosphere; |Large scale 3: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / water; 2-methyl tetrahydrofuran / 16 h / 74 °C / |Inert atmosphere; |Large scale View Scheme

1: sulfuric acid / methanol / 18 h / 65 °C / |Large scale 2: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / 2-methyl tetrahydrofuran / 1 h / 60 - 77 °C / |Inert atmosphere; |Large scale 3: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / water; 2-methyl tetrahydrofuran / 16 h / 74 °C / |Inert atmosphere; |Large scale 4: sodium hydroxide / water; 2-methyl tetrahydrofuran / 1.5 h / 72 °C / |Large scale 5: N-ethyl-N,N-diisopropylamine; 1-propanephosphonic acid cyclic anhydride / dichloromethane / 18 h / 12 - 44 °C / |Large scale View Scheme

1: in N,N-dimethyl-formamide T=20°C; 0.166667 h; Inert atmosphere; 2: With anhydrous iron chloride; caesium carbonate; L-proline in N,N-dimethyl-formamide Microwave irradiationInert atmosphere;

1: sulfuric acid / methanol / 18 h / 65 °C / |Large scale 2: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / 2-methyl tetrahydrofuran / 1 h / 60 - 77 °C / |Inert atmosphere; |Large scale 3: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / water; 2-methyl tetrahydrofuran / 16 h / 74 °C / |Inert atmosphere; |Large scale 4: sodium hydroxide / water; 2-methyl tetrahydrofuran / 1.5 h / 72 °C / |Large scale View Scheme

1.1: copper(l) iodide; potassium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 40 °C 1.2: 20 °C 2.1: sodium hydroxide / dichloromethane; water / 1 h / 20 °C 2.2: 1 h / 0 - 10 °C 2.3: 1 h / 0 - 15 °C View Scheme