1: With isopropylmagnesium chloride in tetrahydrofuran T=-78 - -40°C; 1 h; 2: With water; ammonium chloride in tetrahydrofuran

4-(N,N-dimethlyamino)pyridine; triethylamine; p-toluenesulfonyl chloride in dichloromethane T=20°C; 26 h;

triethylamine in methanol; dichloromethane

n-butyllithium; 1,10-phenanthroline in tetrahydrofuran; hexane T=-78°C; 1 h; Inert atmosphere;

1: 1-methyl-1H-imidazole / tetrahydrofuran / 0 °C / |Inert atmosphere 2: 1,10-phenanthroline; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / |Inert atmosphere View Scheme

1: N,N'-dimethyl-N,N'-propyleneurea; lithium diisopropyl amide / tetrahydrofuran / -40 - 0 °C / |Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C / |Inert atmosphere 3: 1-methyl-1H-imidazole / tetrahydrofuran / 0 °C / |Inert atmosphere 4: 1,10-phenanthroline; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / |Inert atmosphere View Scheme

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C / |Inert atmosphere 2: 1-methyl-1H-imidazole / tetrahydrofuran / 0 °C / |Inert atmosphere 3: 1,10-phenanthroline; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / |Inert atmosphere View Scheme

1: triphenylphosphine; bromine; triethylamine / dichloromethane / 50 h / 0 - 20 °C / |Inert atmosphere 2: N,N'-dimethyl-N,N'-propyleneurea; lithium diisopropyl amide / tetrahydrofuran / -40 - 0 °C / |Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C / |Inert atmosphere 4: 1-methyl-1H-imidazole / tetrahydrofuran / 0 °C / |Inert atmosphere 5: 1,10-phenanthroline; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / |Inert atmosphere View Scheme

1.1: tetrahydrofuran / 20 °C / Reflux 1.2: 0 °C 2.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C 2.2: 0 °C 3.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0 °C View Scheme

1.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C 1.2: 0 °C 2.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0 °C View Scheme