copper(II) tris(triflyl)methide; methoxybenzene T=154°C; debenzylation; 4.5 h;

1.1: phosphorus pentachloride / dichloromethane / -11 - 19 °C 1.2: 7 h / -6 - 20 °C 2.1: potassium carbonate; triphenylphosphine / dichloro(1,5-cyclooctadiene)ruthenium(II) polymer / 1-methyl-pyrrolidin-2-one / 2 h / 140 °C / Inert atmosphere 3.1: sodium methylate / methanol / 1.5 h / 20 °C 4.1: phosphorus tribromide / tetrahydrofuran / 5.5 h / 0 - 20 °C 5.1: potassium carbonate / acetonitrile / 6 h / Reflux; Inert atmosphere 6.1: hydrogenchloride / methanol / 3.22 h / 3 - 9 °C 7.1: SnCl2·2H2O / methanol / 2 h / Reflux 8.1: acetic acid / 1 h / 90 °C 9.1: sodium hydroxide / methanol / 2 h / 90 °C 10.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 65 °C 11.1: ammonium formate / 5 palladium on charcoal / isopropyl alcohol; water / 17 h / 40 - 50 °C View Scheme

1.1: phosphorus pentachloride / dichloromethane / -11 - 19 °C 1.2: 7 h / -6 - 20 °C 2.1: potassium carbonate; triphenylphosphine / dichloro(1,5-cyclooctadiene)ruthenium(II) polymer / 1-methyl-pyrrolidin-2-one / 2 h / 140 °C / Inert atmosphere 3.1: sodium methylate / methanol / 1.5 h / 20 °C 4.1: phosphorus tribromide / tetrahydrofuran / 5.5 h / 0 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 2 h / 85 °C 6.1: pyridine / toluene / 35 h / 20 °C / Inert atmosphere 7.1: hydrogenchloride; hydrogen / palladium on activated charcoal / methanol / 5 h / 20 °C / 3450.35 - 4875.49 Torr 7.2: 120 h View Scheme

1.1: phosphorus pentachloride / dichloromethane / 1.18 h / -16 - 17 °C 1.2: 8.2 h / -10 - 20 °C 2.1: 1-methyl-pyrrolidin-2-one; [Ru(COD)(Cl2)]2; triphenylphosphine / 2 h / 140 °C 3.1: methanol; sodium methylate / 1.5 h / 20 °C 4.1: phosphorus tribromide / tetrahydrofuran / 5.5 h / 0 - 20 °C 5.1: potassium carbonate / N,N-dimethyl acetamide / 8 h / -10 - 20 °C 6.1: methoxybenzene; trifluoroacetic acid / 13 h / 20 - 80 °C View Scheme

1.1: phosphorus pentachloride / dichloromethane / 1.18 h / -16 - 17 °C 1.2: 8.2 h / -10 - 20 °C 2.1: 1-methyl-pyrrolidin-2-one; [Ru(COD)(Cl2)]2; triphenylphosphine / 2 h / 140 °C 3.1: methanol; sodium methylate / 1.5 h / 20 °C 4.1: phosphorus tribromide / tetrahydrofuran / 5.5 h / 0 - 20 °C 5.1: potassium carbonate / N,N-dimethyl acetamide / 8 h / -10 - 20 °C 6.1: methoxybenzene; trifluoroacetic acid / 13 h / 20 - 80 °C 7.1: sodium tetrahydroborate; sodium hydroxide / water / 4.42 h / 5 - 20 °C View Scheme

potassium fluoride; (NH4)2S2O8; CuSO4‵5H2O; silver nitrate in water T=20°C; 6 h; Inert atmosphere;