1: phenol With potassium hydroxide in toluene T=50°C; 0.166667 h; 2: With carbon dioxide T=190°C; P=19001.3 Torr; 2 h; Inert atmosphereAutoclave; 3: 3-iodo-α,α,α-trifluorotoluene With PEPPSI-IPr catalyst; acetic acid; silver carbonate T=130°C; P=19001.3 Torr; 16 h; Inert atmosphereAutoclave; Reagent/catalyst; regioselective reaction;

hydrogen iodide 7.5 h; Heating;

1: 93 percent / aq. Na2CO3; Pd(PPh3)4 / ethanol; toluene / 3 h / Heating 2: 82 percent / aq. HI / 7.5 h / Heating View Scheme

1: 93 percent / aq. Na2CO3; Pd(PPh3)4 / ethanol; toluene / 3 h / Heating 2: 82 percent / aq. HI / 7.5 h / Heating View Scheme

1: [Pd(CH3CN)4](BF4)2; 6,6'-dimethyl-2,2'-bipyridine; anthraquinone-2-sulfonic acid sodium salt; oxygen / 1-methyl-pyrrolidin-2-one / 4 h / 50 °C / 760.05 Torr 2: dimethyl sulfoxide; 1-methyl-pyrrolidin-2-one / 32 h / 80 °C View Scheme