1.1: nBuLi / hexane; tetrahydrofuran / 1 h / -78 °C 1.2: tri-n-butyl borate / hexane; tetrahydrofuran / 2 h / -78 °C 2.1: 13.3 g / aq. Na2CO3 / Pd(PPh3)4 / hexane; tetrahydrofuran / 4.5 h / Heating 3.1: 96 percent / p-toluenesulfonic acid monohydrate / benzene / 7 h / Heating 4.1: nBuLi / hexane; tetrahydrofuran / 1 h / -78 °C 4.2: 76 percent / hexane; tetrahydrofuran / 6 h / -78 °C 5.1: 98 percent / pyridinium tosylate; water / acetone / 16 h / Heating View Scheme

1: With n-butyllithium in tetrahydrofuran T=-78°C; Inert atmosphere; 2: With tri-isopropoxy-borane in tetrahydrofuran T=-78 - 20°C; 1 h; Inert atmosphere; 3: With water Inert atmosphere;

CH3(CH2)3Li in diethyl ether; hexane (under N2); soln. of CH3(CH2)3Li in hexane added to ether soln. of ligand at -78°C, stirred for 30 min, B-compound added, warmed to room temp., aq. HCl added; extd. with aq. NaOH, neutralized with aq. HCl, residue washed, filtered,dried;

hydrogenchloride; n-butyllithium; carbon dioxide in tetrahydrofuran; cyclohexane

1: 2-methyl-3,5-dibromothiophene With n-butyllithium T=-78°C; 2: carbon dioxide

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in tetrahydrofuran; water Suzuki coupling; Inert atmosphereReflux;

1.1: nBuLi / hexane; tetrahydrofuran / 1 h / -78 °C 1.2: tri-n-butyl borate / hexane; tetrahydrofuran / 2 h / -78 °C 2.1: 13.3 g / aq. Na2CO3 / Pd(PPh3)4 / hexane; tetrahydrofuran / 4.5 h / Heating 3.1: 96 percent / p-toluenesulfonic acid monohydrate / benzene / 7 h / Heating View Scheme

sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethanol; water; toluene 16 h; Heating;

1.1: n-BuLi / diethyl ether; hexane / 0.5 h / -78 °C 1.2: 85.5 percent / boric acid tributyl ester / diethyl ether; hexane / -78 - 20 °C 2.1: 70 percent / Na2CO3 / Pd(PPh3)4 / tetrahydrofuran / 70 °C View Scheme