copper diacetate; sodium carbonate; ethylene glycol in isopropyl alcohol T=85°C; Ullmann Condensation; 16 h; Inert atmosphere;

copper(l) iodide; cesium fluoride; N-methyl-2-(methylamino)ethylamine in tetrahydrofuran T=25°C; 18 - 24 h; Inert atmosphere;

tBu2P-N=P(iBuPCH2CH2)3N; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate in toluene T=80°C; 6 h; Inert atmosphere;

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C / |Inert atmosphere 2: caesium carbonate; palladium diacetate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene / para-xylene / 3 h / 125 °C / |Inert atmosphere View Scheme

1.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / ethanol / 6 h / |Reflux; |Inert atmosphere 2.1: hydrazine hydrate / methanol / 2 h / 20 °C 3.1: hydrogenchloride; sodium nitrite / tetrahydrofuran; water / 0.33 h / |Cooling with ice 3.2: 20 °C / |Cooling with ice 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C 5.1: copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / |Inert atmosphere View Scheme

1.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / ethanol / 6 h / |Reflux; |Inert atmosphere 2.1: hydrazine hydrate / methanol / 2 h / 20 °C 3.1: hydrogenchloride; sodium nitrite / tetrahydrofuran; water / 0.33 h / |Cooling with ice 3.2: 20 °C / |Cooling with ice 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C 5.1: copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / |Inert atmosphere View Scheme

1.1: hydrazine hydrate / methanol / 2 h / 20 °C 2.1: hydrogenchloride; sodium nitrite / tetrahydrofuran; water / 0.33 h / |Cooling with ice 2.2: 20 °C / |Cooling with ice 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C 4.1: copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / |Inert atmosphere View Scheme

1.1: hydrogenchloride; sodium nitrite / tetrahydrofuran; water / 0.33 h / |Cooling with ice 1.2: 20 °C / |Cooling with ice 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C 3.1: copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / |Inert atmosphere View Scheme

T=210°C;