sodium hydride in tetrahydrofuran T=20°C;

manganese triacetate in acetic acid T=70°C; 3 h;

1: 3-iodoindole-1-carboxylic acid diethylamide With isopropylmagnesium chloride lithium chloride complex in tetrahydrofuran T=0°C; 0.2 h; 2: benzaldehyde in tetrahydrofuran T=0°C; 0.116667 h;

1: 3-iodoindole-1-carboxylic acid diethylamide With isopropylmagnesium chloride lithium chloride complex in tetrahydrofuran T=0°C; 0.2 h; 2: acetaldehyde in tetrahydrofuran T=0°C; 0.116667 h;

1: 3-iodoindole-1-carboxylic acid diethylamide With isopropylmagnesium chloride lithium chloride complex in tetrahydrofuran T=0°C; 0.2 h; 2: pentanal in tetrahydrofuran T=0°C; 0.116667 h;

1: 1) t-butyllithium / 1) -70 degC, 1 h, 2) -70 degC, 4 to 5 h 2: 41 percent / p-toluenesulphonic acid / toluene / 6.5 h / Heating 3: 1) n-butyllithium / 1) hexane/THF, -70 degC, 15-30 min, 2a) -70 to -30 degC, 1 h, 2b) r.t., 30 min 4: 41 percent / bis(trifluoroacetoxy)iodobenzene / acetonitrile; H2O / 0.75 h / Ambient temperature 5: 65 percent / 25percent aq. sodium hydroxide / ethanol / 16 h / Heating View Scheme

1.1: 84 percent / tert-butyllithium / hexane; tetrahydrofuran / 3 h / -78 °C 2.1: s-butyllithium; TMEDA / tetrahydrofuran; hexane / -78 °C 2.2: B(O-iPr)3 / tetrahydrofuran; hexane / -78 - 20 °C 2.3: 60 percent / hexane; ethyl acetate; tetrahydrofuran 3.1: 94 percent / Pd(PPh3)4; K3PO4 / dimethylformamide / 17 h / 80 °C 4.1: 71 percent / potassium tert-butylate / tetrahydrofuran / Heating View Scheme

1.1: 84 percent / tert-butyllithium / hexane; tetrahydrofuran / 3 h / -78 °C 2.1: s-butyllithium; TMEDA / tetrahydrofuran; hexane / 3 h / -78 °C 2.2: 81 percent / tetrahydrofuran; hexane / -78 - 20 °C 3.1: 75 percent / KOH / ethanol / 12 h / Heating View Scheme

tert.-butyl lithium in tetrahydrofuran; hexane T=-78°C; 3 h;