hydrogen; palladium on activated charcoal in methanol 3 h;

palladium diacetate; caesium carbonate; triphenylphosphine in o-xylene T=143°C; 1 h;

potassium phosphate; [(P{(NC5H10)(C6H11)2})2Pd(Cl)2] in toluene T=80°C; Suzuki-Miyaura cross-coupling reaction; 0.5 h; Air;

[(P{(NC5H10)(C6H11)2})2Pd(Cl)2] in tetrahydrofuran; 1-methyl-pyrrolidin-2-one T=100°C; Negishi cross-coupling reaction; 2 h; In air;

hydrogenchloride in methanol electrolysis;

hydrogenchloride in methanol electrolysis;

hydrogenchloride in methanol electrolysis;

hydrogenchloride in methanol electrolysis;

hydrogenchloride in methanol electrolysis;

1: 1.) N-methylmorpholin, 1-hydroxybenzotriazole; 2.) N,N'-dicyclohexylcarbodiimide / 1.) CH2Cl2; 2.) CH2Cl2, 30 min, 0 deg C; 12 h at room temp. 2: 97 percent / 1 N HCl, H2 / Pd/10percent on charcoal / methanol / 4 h 3: 89 percent / 2,6-dimethylpyridine; tetraethylammonium tetrafluoroborate / CH2Cl2 / 8 h / anodic oxidation 4: 60 percent / 1 N NaOH / methanol / 4 h 5: 1.) N-methylmorpholin, 1-hydroxybenzotriazole; 2.) N,N'-dicyclohexylcarbodiimide / 1.) CH2Cl2; 2.) CH2Cl2, 1 h, 0 deg C; 24 h at room temp. 6: 90 percent / 1 N HCl, H2 / Pd/10percent on charcoal / methanol / 4 h 7: 59 percent / 2,6-dimethylpyridine; tetraethylammonium tetrafluoroborate / CH2Cl2 / 8 h / anodic oxidation 8: 57 percent / 1 N NaOH / methanol / 4 h 9: 1.) N-methylmorpholin, 1-hydroxybenzotriazole; 2.) N,N'-dicyclohexylcarbodiimide / 1.) CH2Cl2, 0 deg C; 2.) CH2Cl2, 1 h, 0 deg C; 12 h at room temp. 10: 90 percent / H2 / Pd/10percent on charcoal / methanol / 3 h View Scheme