1: With n-butyllithium in diethyl ether; hexane; toluene T=-40 - -5°C; 1 h; 2: With tri-isopropoxy-borane in diethyl ether; hexane; toluene T=20°C; 4 h; 3: With hydrogenchloride in diethyl ether; hexane; water; toluene

1: 2-bromo-6-phenyl-naphthalene With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 2.33333 h; Inert atmosphere; 2: boric acid trimethyl ester in tetrahydrofuran; hexane T=20°C; 20 h; 3: With hydrogenchloride in tetrahydrofuran; hexane; water 0.5 h;

sodium chloride in hexane; toluene

sodium chloride; sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in toluene

1.1: n-butyllithium / hexane; tetrahydrofuran / 2.33 h / -78 °C / Inert atmosphere 1.2: 18 h / 20 °C 1.3: 1 h 2.1: potassium carbonate / palladium diacetate; tris-(o-tolyl)phosphine / toluene; ethanol; water / 5 h / 85 °C / Inert atmosphere; Reflux 3.1: n-butyllithium / hexane; tetrahydrofuran / 2.33 h / -78 °C / Inert atmosphere 3.2: 20 h / 20 °C 3.3: 0.5 h View Scheme

1.1: potassium carbonate / palladium diacetate; tris-(o-tolyl)phosphine / toluene; ethanol; water / 5 h / 85 °C / Inert atmosphere; Reflux 2.1: n-butyllithium / hexane; tetrahydrofuran / 2.33 h / -78 °C / Inert atmosphere 2.2: 20 h / 20 °C 2.3: 0.5 h View Scheme