N-ethyl-N,N-diisopropylamine; palladium diacetate; tris-(o-tolyl)phosphine in N,N-dimethyl-formamide T=95 - 100°C; Inert atmosphere;

water; potassium carbonate in methanol T=20 - 40°C; Product distribution / selectivity;

1.1: N,N-dimethyl-formamide / 95 - 100 °C 1.2: 0 - 5 °C / pH 8 - 9 2.1: N-ethyl-N,N-diisopropylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 90 - 95 °C / Inert atmosphere 3.1: water; sodium carbonate; methanol / 2 h / 25 - 30 °C View Scheme

1: N-ethyl-N,N-diisopropylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 90 - 95 °C / Inert atmosphere 2: water; sodium carbonate; methanol / 2 h / 25 - 30 °C View Scheme

1.1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 3 h / Reflux 2.1: ethylmagnesium bromide; zinc(II) chloride / dichloromethane; tetrahydrofuran / 5 - 30 °C 2.2: -10 - 25 °C 3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 10 - 50 °C / Inert atmosphere; Darkness 3.2: 0 - 35 °C / pH 12 - 13 4.1: N,N-dimethyl-formamide / 95 - 100 °C 4.2: 0 - 5 °C / pH 8 - 9 5.1: N-ethyl-N,N-diisopropylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 90 - 95 °C / Inert atmosphere 6.1: water; sodium carbonate; methanol / 2 h / 25 - 30 °C View Scheme

1.1: ethylmagnesium bromide; zinc(II) chloride / dichloromethane; tetrahydrofuran / 5 - 30 °C 1.2: -10 - 25 °C 2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 10 - 50 °C / Inert atmosphere; Darkness 2.2: 0 - 35 °C / pH 12 - 13 3.1: N,N-dimethyl-formamide / 95 - 100 °C 3.2: 0 - 5 °C / pH 8 - 9 4.1: N-ethyl-N,N-diisopropylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 90 - 95 °C / Inert atmosphere 5.1: water; sodium carbonate; methanol / 2 h / 25 - 30 °C View Scheme

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 10 - 50 °C / Inert atmosphere; Darkness 1.2: 0 - 35 °C / pH 12 - 13 2.1: N,N-dimethyl-formamide / 95 - 100 °C 2.2: 0 - 5 °C / pH 8 - 9 3.1: N-ethyl-N,N-diisopropylamine / palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 90 - 95 °C / Inert atmosphere 4.1: water; sodium carbonate; methanol / 2 h / 25 - 30 °C View Scheme

methanol; sodium hydroxide T=60 - 65°C;

1.1: triethylamine / N,N-dimethyl-formamide / 2 h / 90 - 100 °C 1.2: 3 h / Reflux 2.1: water; sodium carbonate; methanol / 2 h / 25 - 30 °C View Scheme

1: triethylamine; 4-(N,N-dimethlyamino)pyridine / toluene / 0.25 h 2: tris-(o-tolyl)phosphine; triethylamine; palladium diacetate / N,N-dimethyl-formamide / 0.25 h / 25 - 120 °C 3: sodium hydroxide; methanol / 60 - 65 °C View Scheme