lithium aluminium tetrahydride in tetrahydrofuran T=20°C; 0.75 h;

sodium carbonate; bis(dibenzylideneacetone)-palladium(0); dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine in 1,4-dioxane; water Suzuki-Miyaura cross-coupling; 48 h; Inert atmosphereReflux;

12-tungstophosphoric acid immobilized on [bmim][FeCl4] T=75 - 82°C; 0.00972222 h; Microwave irradiation;

1: sodium carbonate; bis(dibenzylideneacetone)-palladium(0); dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine / 1,4-dioxane; water / 5 h / Inert atmosphere; Reflux 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C 3: sodium carbonate; bis(dibenzylideneacetone)-palladium(0); dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine / 1,4-dioxane; water / 48 h / Inert atmosphere; Reflux View Scheme

1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C 2: sodium carbonate; bis(dibenzylideneacetone)-palladium(0); dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine / 1,4-dioxane; water / 5 h / Inert atmosphere; Reflux 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C 4: sodium carbonate; bis(dibenzylideneacetone)-palladium(0); dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine / 1,4-dioxane; water / 48 h / Inert atmosphere; Reflux View Scheme

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C 2: sodium carbonate; bis(dibenzylideneacetone)-palladium(0); dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphine / 1,4-dioxane; water / 48 h / Inert atmosphere; Reflux View Scheme

sodium hydride 1) THF, 0 deg C, 10 min then RT, 1 h, 2) THF, 0 deg C, 30 min then 50 deg C, 1 h and RT, 24 h; Yield given. Multistep reaction;

12-tungstophosphoric acid immobilized on [bmim][FeCl4] T=120 - 130°C; 0.025 h; Microwave irradiation;