N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile in tetrachloromethane Heating / reflux;

1.1: N-bromosuccinmide; 1,1'-azobis (cyclohexanecarbonitrile) / α,α,α-trifluorotoluene / 18 h / Inert atmosphere; Reflux 2.1: N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere 3.1: water; sodium hydroxide / methanol / 4 h 4.1: toluene-4-sulfonic acid / dichloromethane / 15 h / 20 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran / 0.17 h / -98 °C / Inert atmosphere 5.2: 1.67 h / -98 - 20 °C / Inert atmosphere 6.1: water / tetrahydrofuran / 1 h / 20 °C 7.1: magnesium sulfate / dichloromethane / 15 h / 20 °C / Inert atmosphere 8.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / -78 °C / Inert atmosphere 8.2: -98 - -78 °C / Inert atmosphere 9.1: toluene-4-sulfonic acid / diethyl ether / Inert atmosphere; Reflux 10.1: water; sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 16 h / 20 °C View Scheme

ammonium chloride in methanol; dichloromethane; toluene

1.1: N-bromosuccinmide; 1,1'-azobis (cyclohexanecarbonitrile) / α,α,α-trifluorotoluene / 18 h / Inert atmosphere; Reflux 2.1: N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere 3.1: water; sodium hydroxide / methanol / 4 h 4.1: toluene-4-sulfonic acid / dichloromethane / 15 h / 20 °C / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran / 0.17 h / -98 °C / Inert atmosphere 5.2: 1.67 h / -98 - 20 °C / Inert atmosphere 6.1: water / tetrahydrofuran / 1 h / 20 °C 7.1: magnesium sulfate / dichloromethane / 15 h / 20 °C / Inert atmosphere 8.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / -78 °C / Inert atmosphere 8.2: -98 - -78 °C / Inert atmosphere 9.1: toluene-4-sulfonic acid / diethyl ether / Inert atmosphere; Reflux View Scheme

Pd(CH2SiMe3)2(cod); cyclohexyl BrettPhos; silver fluoride in toluene T=130°C; 18 h; Darkness;

cesium hydroxide monohydrate; Pd(CH2SiMe3)2(cod); 2-(di-1-adamantylphosphanyl)-1-(2,6-diisopropylphenyl)-1H-imidazole in tetrahydrofuran T=24°C; 20 h; Inert atmosphere;

silver fluoride; Pd(CH2SiMe3)2(cod); cyclohexyl BrettPhos in toluene T=130°C; 18 h; Sealed tube;

in toluene T=100°C; Sealed tube;

Pd(CH2SiMe3)2(cod); cyclohexyl BrettPhos; silver fluoride in toluene T=130°C; 18 h; Darkness;

hydrogenchloride in diethyl ether