cesium fluoride; Na2[PdCl4] in methanol T=40°C; Arylation; cross-coupling; 24 h;

palladium diacetate; sodium carbonate; triphenylphosphine in water; acetone Suzuki Coupling; 12 h; Inert atmosphereReflux;

sodium acetate

sodium hydroxide

1.1: Mg; I2 / tetrahydrofuran / Heating 1.2: 60 percent / tetrahydrofuran / -40 - 0 °C 2.1: Et3SiH; TFA / 0 - 20 °C View Scheme

1.1: Mg; I2 / tetrahydrofuran / Heating 1.2: 60 percent / tetrahydrofuran / -40 - 0 °C 2.1: Et3SiH; TFA / 0 - 20 °C 3.1: (COCl)2; DMF / CH2Cl2 / -10 - 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -70 - -50 °C 4.2: 91 percent / tetrahydrofuran; hexane / -70 - 0 °C 5.1: NaN(SiMe3)2 / tetrahydrofuran / 1 h / -75 °C 5.2: 61 percent / tetrahydrofuran / -70 - -50 °C 6.1: 97 percent / aq. H2O2; LiOH / tetrahydrofuran / 0 - 20 °C View Scheme

1.1: Mg; I2 / tetrahydrofuran / Heating 1.2: 60 percent / tetrahydrofuran / -40 - 0 °C 2.1: Et3SiH; TFA / 0 - 20 °C 3.1: (COCl)2; DMF / CH2Cl2 / -10 - 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -70 - -50 °C 4.2: 91 percent / tetrahydrofuran; hexane / -70 - 0 °C 5.1: NaN(SiMe3)2 / tetrahydrofuran / 1 h / -75 °C 5.2: 61 percent / tetrahydrofuran / -70 - -50 °C 6.1: 97 percent / aq. H2O2; LiOH / tetrahydrofuran / 0 - 20 °C 7.1: 99 percent / N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; i-Pr2NEt; 1-hydroxy-1,2,3-benzotriazole hydrate / CH2Cl2 / 4 - 20 °C 8.1: 80 percent / TFA / CH2Cl2 / 2 h / 20 °C View Scheme

1.1: Mg; I2 / tetrahydrofuran / Heating 1.2: 60 percent / tetrahydrofuran / -40 - 0 °C 2.1: Et3SiH; TFA / 0 - 20 °C 3.1: (COCl)2; DMF / CH2Cl2 / -10 - 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -70 - -50 °C 4.2: 91 percent / tetrahydrofuran; hexane / -70 - 0 °C 5.1: NaN(SiMe3)2 / tetrahydrofuran / 1 h / -75 °C 5.2: 61 percent / tetrahydrofuran / -70 - -50 °C 6.1: 97 percent / aq. H2O2; LiOH / tetrahydrofuran / 0 - 20 °C 7.1: 99 percent / N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; i-Pr2NEt; 1-hydroxy-1,2,3-benzotriazole hydrate / CH2Cl2 / 4 - 20 °C View Scheme