n-butyllithium in diethyl ether react. with BuLi/TMEDA at 0°C, followed by B(OMe)3;

1: With n-butyllithium; N,N,N',N,-tetramethylethylenediamine in diethyl ether; hexane T=0°C; 1 h; 2: With boric acid trimethyl ester in diethyl ether; hexane T=0 - 20°C; 3: With hydrogenchloride in diethyl ether; hexane pH=6; Further stages.;

1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1 h; 2: With triisopropyl borate 3: With hydrogenchloride in water; ethyl acetate

2: H2O2, aq. NaOH View Scheme

potassium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; water Suzuki cross-coupling reaction; 18 h; Heating;

potassium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; water Suzuki cross-coupling reaction; 18 h; Heating;

1: palladium(II) dichloride bis[bis(diphenylphosphine)ferrocene]; caesium carbonate / tetrahydrofuran / |Reflux 2: tetrabutyl ammonium fluoride / tetrahydrofuran 3: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 20 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 5: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C 6: sodium hydride / tetrahydrofuran / 0 °C 7: o-hydroxynitrobenzene / 144 h / 130 °C / |Inert atmosphere 8: sodium hydroxide / methanol; water / 80 °C 9: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C 10: Dess-Martin periodane / dichloromethane 11: boron trifluoride diethyl etherate / dichloromethane / 3 h / -10 °C 12: diphenylchlorosilane; indium(III) chloride / 1,2-dichloro-ethane / 21 h / |Reflux 13: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 14: (1S)-10-camphorsulfonic acid / tetrahydrofuran / |Reflux 15: lithium aluminium tetrahydride / 1,4-dioxane / |Reflux 16: Dess-Martin periodane / dichloromethane / 2.5 h / 0 - 20 °C View Scheme

1: palladium(II) dichloride bis[bis(diphenylphosphine)ferrocene]; caesium carbonate / tetrahydrofuran / |Reflux 2: tetrabutyl ammonium fluoride / tetrahydrofuran 3: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 20 °C 4: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 5: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C 6: sodium hydride / tetrahydrofuran / 0 °C 7: o-hydroxynitrobenzene / 144 h / 130 °C / |Inert atmosphere 8: sodium hydroxide / methanol; water / 80 °C 9: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C 10: Dess-Martin periodane / dichloromethane 11: boron trifluoride diethyl etherate / dichloromethane / 3 h / -10 °C 12: diphenylchlorosilane; indium(III) chloride / 1,2-dichloro-ethane / 21 h / |Reflux 13: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 14: (1S)-10-camphorsulfonic acid / tetrahydrofuran / |Reflux 15: Dess-Martin periodane / dichloromethane / 5.5 h / 0 - 20 °C 16: lithium aluminium tetrahydride / 1,4-dioxane / 6 h / |Reflux View Scheme

1: 61 percent / aq. Na2CO3 / Pd(PPh3)4 / toluene; ethanol / Heating 2: 100 percent / BBr3 / CH2Cl2 / 20 °C View Scheme

1: 76 percent / aq. Na2CO3 / Pd(PPh3)4 / tetrahydrofuran / 13 h / Heating 2: 64 percent / BBr3 / CH2Cl2 / -78 - 20 °C View Scheme