manganese(IV) oxide in diethyl ether 2 h;

1: 2-chloro-4-phenyl-1-buten-3-yne With lithium diisopropyl amide in tetrahydrofuran; hexane T=-78 - -30°C; 1 h; Inert atmosphere; 2: With zinc dibromide in tetrahydrofuran; hexane T=-30 - 0°C; 0.5 h; Inert atmosphere; 3: trans-3-iodo-2-propen-1-ol With tetrakis(triphenylphosphine) palladium(0); diethylzinc in tetrahydrofuran; hexane; N,N-dimethyl-formamide T=0 - 60°C; Negishi Coupling; 6 h; Inert atmosphere;

1.1: tetrakis(triphenylphosphine) palladium(0) / benzene / 0.25 h / 23 °C / |Inert atmosphere 1.2: 5 h / |Inert atmosphere 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1 h / -78 - -30 °C / |Inert atmosphere 2.2: 0.5 h / -30 - 0 °C / |Inert atmosphere 2.3: 6 h / 0 - 60 °C / |Inert atmosphere View Scheme

hydroxylamine hydrochloride; ethylamine; copper(l) chloride in methanol

ethylamine; copper(l) chloride

air; ammonium chloride; copper(l) chloride Reagens 4: FeCl3; Reagens 5: H2O;

pyridine