1.1: 0.5 h / Inert atmosphere 2.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; zinc(II) chloride; zinc / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere 3.1: potassium hydroxide / aacetone / 2 h / Reflux; Inert atmosphere 4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 2 h / Inert atmosphere; Reflux 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere 5.2: 20 °C View Scheme

1: 891 mg / Et3N / CH2Cl2 / 0.83 h / 20 °C 2: 96 percent / NaH / dimethylformamide / 1.5 h / 20 °C 3: 94 percent / Ag2CO3 / Pd(OAc)2; P(o-Tol)3 / dimethylformamide / 0.33 h / Heating View Scheme

1: 83 percent / Et3N / tetrahydrofuran / 12 h / Ambient temperature 2: 89 percent / CuI, Et3N / PdCl2(PPh3)2 / 6 h / Ambient temperature 3: 95 percent / K2CO3 / methanol / 0.5 h / Ambient temperature 4: 61 percent / n-Bu3SnH, AIBN / benzene / 5 h / Heating View Scheme

1: 75 percent / triethylamine / benzene / Heating 2: 55 percent / K2CO3 / Pd(OAc)2, TPP, Et4NCl / dimethylformamide / 4 h / Ambient temperature View Scheme