1,10-phenanthroline; Cu(OTf)2; lithium hydroxide hydrate in dichloromethane T=80°C; 48 h; AirSealed tube;

[Ni0(1,5-cyclooctadiene)2]; dimethyl zinc; tri-cyclo-hexyl-phosphine in ethylene glycol dimethyl ether; toluene T=40°C; 12 h; Inert atmosphere;

potassium hydroxide in ethanol; water 18 h; Heating;

in tetrahydrofuran T=0°C; 1 h;

1.1: sodium hydride / tetrahydrofuran / 0 - 20 °C 1.2: 0 - 20 °C 2.1: [Ni0(1,5-cyclooctadiene)2]; dimethyl zinc; tri-cyclo-hexyl-phosphine / ethylene glycol dimethyl ether; toluene / 12 h / 40 °C / Inert atmosphere View Scheme

1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 2.1: triethylamine / dichloromethane / 0 - 20 °C 3.1: sodium hydride / tetrahydrofuran / 0 - 20 °C 3.2: 0 - 20 °C 4.1: [Ni0(1,5-cyclooctadiene)2]; dimethyl zinc; tri-cyclo-hexyl-phosphine / ethylene glycol dimethyl ether; toluene / 12 h / 40 °C / Inert atmosphere View Scheme

1.1: triethylamine / dichloromethane / 0 - 20 °C 2.1: sodium hydride / tetrahydrofuran / 0 - 20 °C 2.2: 0 - 20 °C 3.1: [Ni0(1,5-cyclooctadiene)2]; dimethyl zinc; tri-cyclo-hexyl-phosphine / ethylene glycol dimethyl ether; toluene / 12 h / 40 °C / Inert atmosphere View Scheme

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