trifluoroacetic acid in ethyl acetate

1: 3,4-dihydro-2H-pyran; 4-chloro-1H-indazole With pyridinium p-toluenesulfonate in n-heptane; toluene T=40°C; 11 h; Inert atmosphereLarge scale; 2: 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-4',4',5',5'-tetramethyl-1,3,2-dioxaborolane With Ni(NO3)2·6H2O; triethylamine; triphenylphosphine in methanol T=0 - 25°C; 3.5 h; Inert atmosphereLarge scale;

triethylamine; triphenylphosphine; (1,5-cyclooctadiene)(cyclopentadienyl)nickel in methanol T=25 - 70°C; 4 h; Inert atmosphere; Product distribution / selectivity;

1.1: hydrogen / palladium 10 on activated carbon / ethanol / 20 °C / Inert atmosphere 2.1: hydrogenchloride; sodium nitrite / water / -5 °C 2.2: 0.17 h 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / methanol / 20 °C 4.1: trifluoroacetic acid / ethyl acetate View Scheme

1.1: sodium nitrite / water; acetic acid / 2 h / 20 °C 2.1: hydrogen / palladium 10 on activated carbon / ethanol / 20 °C / Inert atmosphere 3.1: hydrogenchloride; sodium nitrite / water / -5 °C 3.2: 0.17 h 4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / methanol / 20 °C 5.1: trifluoroacetic acid / ethyl acetate View Scheme

1.1: hydrogenchloride; sodium nitrite / water / -5 °C 1.2: 0.17 h 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / methanol / 20 °C 3.1: trifluoroacetic acid / ethyl acetate View Scheme

1.1: potassium acetate; acetic anhydride / ethylene glycol dimethyl ether / 6 h / 20 °C / |Inert atmosphere; |Large scale 1.2: 15 h / 60 °C / |Inert atmosphere; |Large scale 1.3: 0 °C / |Inert atmosphere; |Large scale 2.1: pyridinium p-toluenesulfonate / toluene; n-heptane / 11 h / 40 °C / |Inert atmosphere; |Large scale 2.2: 3.5 h / 0 - 25 °C / |Inert atmosphere; |Large scale View Scheme