1,1'-bis-(di-tert-butylphosphino)ferrocene; triethylamine; bis(dibenzylideneacetone)-palladium(0) in 1,4-dioxane T=100°C; 24 h; Inert atmosphere;

Et3N; tetrabutylammonium iodide; DiPPF; bis(dibenzylideneacetone)-palladium(0) in 1,4-dioxane 100°C, 24 h; GC;

1,1'-bis-(di-tert-butylphosphino)ferrocene; triethylamine; bis(dibenzylideneacetone)-palladium(0) in 1,4-dioxane T=100°C; 24 h; Inert atmosphere;

1.1: formic acid; sulfuric acid / acetic acid 2.1: thionyl chloride / N,N-dimethyl-formamide / toluene / 5 h / 65 - 70 °C 3.1: iron(III) sulfate pentahydrate; iron / toluene / 99 - 114 °C 3.2: 62 - 66 °C / Inert atmosphere 4.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / 6 h / Reflux 4.2: 20 °C 5.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 16 h / 20 °C 5.2: 2 - 51 °C 6.1: boron trichloride / dichloromethane / 52.25 h / 2 - 20 °C 6.2: 1.08 h / 12 °C / Reflux View Scheme

acetic acid Product distribution / selectivity;

1.1: formic acid; sulfuric acid / acetic acid 2.1: thionyl chloride / N,N-dimethyl-formamide / toluene / 5 h / 65 - 70 °C 3.1: iron(III) sulfate pentahydrate; iron / toluene / 99 - 114 °C 3.2: 62 - 66 °C / Inert atmosphere 4.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / 6 h / Reflux 4.2: 20 °C 5.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 16 h / 20 °C 5.2: 2 - 51 °C View Scheme

1.1: formic acid; sulfuric acid / acetic acid 2.1: thionyl chloride / N,N-dimethyl-formamide / toluene / 5 h / 65 - 70 °C 3.1: iron(III) sulfate pentahydrate; iron / toluene / 99 - 114 °C 3.2: 62 - 66 °C / Inert atmosphere 4.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / 6 h / Reflux 4.2: 20 °C 5.1: sodium hydroxide / dichloromethane; water / 6.75 h / 16 - 20 °C / Reflux View Scheme