sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; water T=75°C; 36 h;

water; pyridinium p-toluenesulfonate in acetone 16 h; Heating;

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: 82 percent / N-bromosuccinimide; acetic acid / 5 h / 55 °C 2: 63 percent / Na2CO3 / tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran; H2O / 36 h / 75 °C View Scheme

1.1: 13.3 g / aq. Na2CO3 / Pd(PPh3)4 / hexane; tetrahydrofuran / 4.5 h / Heating 2.1: 96 percent / p-toluenesulfonic acid monohydrate / benzene / 7 h / Heating 3.1: nBuLi / hexane; tetrahydrofuran / 1 h / -78 °C 3.2: 76 percent / hexane; tetrahydrofuran / 6 h / -78 °C 4.1: 98 percent / pyridinium tosylate; water / acetone / 16 h / Heating View Scheme

1.1: 96 percent / p-toluenesulfonic acid monohydrate / benzene / 7 h / Heating 2.1: nBuLi / hexane; tetrahydrofuran / 1 h / -78 °C 2.2: 76 percent / hexane; tetrahydrofuran / 6 h / -78 °C 3.1: 98 percent / pyridinium tosylate; water / acetone / 16 h / Heating View Scheme

1.1: nBuLi / hexane; tetrahydrofuran / 1 h / -78 °C 1.2: 76 percent / hexane; tetrahydrofuran / 6 h / -78 °C 2.1: 98 percent / pyridinium tosylate; water / acetone / 16 h / Heating View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in tetrahydrofuran; diethyl ether; hexane; water; ethylene glycol T=50°C; Reflux;

1: bromine; acetic acid / 16 h / 20 °C 2: n-butyllithium / tetrahydrofuran / -78 - 20 °C 3: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 5 h / Reflux 4: toluene-4-sulfonic acid / benzene / 10 h / Reflux 5: n-butyllithium / tetrahydrofuran / -78 °C 6: pyridinium p-toluenesulfonate / water; acetone / 16 h / Reflux View Scheme

1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 5 h / Reflux 2: toluene-4-sulfonic acid / benzene / 10 h / Reflux 3: n-butyllithium / tetrahydrofuran / -78 °C 4: pyridinium p-toluenesulfonate / water; acetone / 16 h / Reflux View Scheme