1: 3-fluoropyridine With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium in diethyl ether; hexane T=-60°C; 1 h; 2: chloro-trimethyl-silane in diethyl ether; hexane T=-60°C;

n-butyllithium; N,N,N',N,-tetramethylethylenediamine in diethyl ether T=-40°C; 0.5 h; other solvent, temperatures and reaction times, instead of TMEDA with DABCO, LDA and various excess of LDA; Product distribution;

1.1: diisopropylamine; BuLi / tetrahydrofuran; hexane / 2 h / -75 °C 1.2: 78 percent / iodine / tetrahydrofuran; hexane 2.1: LDA / tetrahydrofuran; hexane / 2 h / -75 °C 2.2: H2O / tetrahydrofuran 3.1: tetrahydrofuran / 0.08 h / 0 °C 3.2: tetrahydrofuran / 0.33 h 3.3: 83 percent / NaOH / ethanol; H2O / 0.08 h / Heating View Scheme