sodium hydroxide in ethanol Heating;

boron tribromide in dichloromethane T=-78°C;

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 84 percent / I2 / tetrahydrofuran; hexane / -78 - 20 °C 2.1: NaOH / ethanol / Heating View Scheme

1.1: NaH / tetrahydrofuran / 2 h / 20 °C 1.2: 91 percent / tetrahydrofuran / 8 h / 20 °C 2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 84 percent / iodine / tetrahydrofuran; hexane / -78 - 20 °C 3.1: 89 percent / NaOH / ethanol / Heating View Scheme

1.1: t-Bu2Zn(tmp)Li / tetrahydrofuran / -30 °C 2.1: boron tribromide / dichloromethane / -78 - 20 °C 2.2: 0 - 20 °C View Scheme

1: palladium diacetate; anhydrous lithium acetate / 1,2-dichloro-ethane / 28 h / 80 °C / |Inert atmosphere; |Glovebox; |Schlenk technique 2: hydrogen fluoride / tetrahydrofuran; water / 1 h / 0 - 20 °C 3: N-iodo-succinimide; silver fluoride / tetrahydrofuran / 20 - 70 °C / |Inert atmosphere; |Glovebox; |Darkness 4: caesium carbonate / methanol / 3 h / 0 - 20 °C View Scheme

1: [bis(acetoxy)iodo]benzene; palladium diacetate; N-bromosuccinmide / 1,2-dichloro-ethane / 26 h / 50 °C / |Inert atmosphere; |Glovebox; |Schlenk technique 2: palladium diacetate; anhydrous lithium acetate / 1,2-dichloro-ethane / 28 h / 80 °C / |Inert atmosphere; |Glovebox; |Schlenk technique 3: hydrogen fluoride / tetrahydrofuran; water / 1 h / 0 - 20 °C 4: N-iodo-succinimide; silver fluoride / tetrahydrofuran / 20 - 70 °C / |Inert atmosphere; |Glovebox; |Darkness 5: caesium carbonate / methanol / 3 h / 0 - 20 °C View Scheme

1: potassium phosphate; dirhodium tetraacetate / 1,4-dioxane / 80 - 100 °C / |Inert atmosphere; |Glovebox; |Schlenk technique 2: [bis(acetoxy)iodo]benzene; palladium diacetate; N-bromosuccinmide / 1,2-dichloro-ethane / 26 h / 50 °C / |Inert atmosphere; |Glovebox; |Schlenk technique 3: palladium diacetate; anhydrous lithium acetate / 1,2-dichloro-ethane / 28 h / 80 °C / |Inert atmosphere; |Glovebox; |Schlenk technique 4: hydrogen fluoride / tetrahydrofuran; water / 1 h / 0 - 20 °C 5: N-iodo-succinimide; silver fluoride / tetrahydrofuran / 20 - 70 °C / |Inert atmosphere; |Glovebox; |Darkness 6: caesium carbonate / methanol / 3 h / 0 - 20 °C View Scheme

Diazotization;

1.1: sodium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 1.2: 2 h / 20 °C / Inert atmosphere 2.1: sodium hydroxide / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / N,N-dimethyl-formamide / 3 h / 40 °C / Inert atmosphere 4.1: sodium hydroxide / N,N-dimethyl-formamide / 5 h / 140 °C / Inert atmosphere View Scheme