5 Pd(II)/C(eggshell); hydrogen in methanol T=20°C; 1.5 h;

1: potassium carbonate / acetone / Inert atmosphere; Reflux 2: selenium(IV) oxide / 1,4-dioxane / 5 h / 180 °C / Inert atmosphere; Sealed tube 3: n-butyllithium; triphenyl-methyl-phosphonium iodide / tetrahydrofuran / 3 h / -78 - 20 °C / Inert atmosphere 4: sodium acetate; palladium diacetate / acetonitrile / 0.17 h 5: 5 Pd(II)/C(eggshell); hydrogen / methanol / 1.5 h / 20 °C View Scheme

1: selenium(IV) oxide / 1,4-dioxane / 5 h / 180 °C / Inert atmosphere; Sealed tube 2: n-butyllithium; triphenyl-methyl-phosphonium iodide / tetrahydrofuran / 3 h / -78 - 20 °C / Inert atmosphere 3: sodium acetate; palladium diacetate / acetonitrile / 0.17 h 4: 5 Pd(II)/C(eggshell); hydrogen / methanol / 1.5 h / 20 °C View Scheme

1: [Pd2(dibenzylideneacetone)3]*dibenzylideneacetone; sodium acetate / 1 h / 80 °C / Microwave irradiation 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / Inert atmosphere; Reflux 3: 5 Pd(II)/C(eggshell); hydrogen / methanol / 1.5 h / 20 °C View Scheme

1: sulfuric acid / 0.25 h / 130 °C / Cooling with ice 2: potassium carbonate / acetone / Inert atmosphere; Reflux 3: selenium(IV) oxide / 1,4-dioxane / 5 h / 180 °C / Inert atmosphere; Sealed tube 4: n-butyllithium; triphenyl-methyl-phosphonium iodide / tetrahydrofuran / 3 h / -78 - 20 °C / Inert atmosphere 5: sodium acetate; palladium diacetate / acetonitrile / 0.17 h 6: 5 Pd(II)/C(eggshell); hydrogen / methanol / 1.5 h / 20 °C View Scheme

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / Inert atmosphere; Reflux 2: 5 Pd(II)/C(eggshell); hydrogen / methanol / 1.5 h / 20 °C View Scheme

1: potassium carbonate / acetone / 20 h / 20 °C / Inert atmosphere 2: [Pd2(dibenzylideneacetone)3]*dibenzylideneacetone; sodium acetate / 1 h / 80 °C / Microwave irradiation 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / Inert atmosphere; Reflux 4: 5 Pd(II)/C(eggshell); hydrogen / methanol / 1.5 h / 20 °C View Scheme

1: palladium; aq. NaOH solution / Hydrogenation 2: diethyl ether View Scheme

diethyl ether