1: With hydrogenchloride; sodium nitrite in water T=-15 - 0°C; 0.833333 h; 2: With potassium iodide in water T=20°C; 6.17 h;

N-iodo-succinimide; silver fluoride in tetrahydrofuran T=20°C; Inert atmosphereDarkness;

1: N-bromosuccinmide; [bis(acetoxy)iodo]benzene; palladium diacetate / 1,2-dichloro-ethane / 3.5 h / 70 °C / Inert atmosphere 2: N-iodo-succinimide; silver fluoride / tetrahydrofuran / 20 °C / Inert atmosphere; Darkness View Scheme

1: potassium phosphate; bis(bicyclo[2.2.1]hepta-2,5-diene)dichlorodirhodium / 1,4-dioxane / 20 °C / Inert atmosphere 2: N-bromosuccinmide; [bis(acetoxy)iodo]benzene; palladium diacetate / 1,2-dichloro-ethane / 3.5 h / 70 °C / Inert atmosphere 3: N-iodo-succinimide; silver fluoride / tetrahydrofuran / 20 °C / Inert atmosphere; Darkness View Scheme

1.1: N-bromosuccinmide / chloroform / 3 h / 0 °C / Inert atmosphere 2.1: sulfuric acid; sodium nitrite / water / 2 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere View Scheme

1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate in toluene T=60 - 160°C; 2.33333 h; Microwave irradiation;

1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) in toluene T=140°C; 5 h;

1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 20 °C / Inert atmosphere 2.1: n-butyllithium; N,N,N',N,-tetramethylethylenediamine / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 2.2: 3 h / -78 - 25 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 26 °C / Inert atmosphere View Scheme