1.1: ZnCl2 / tetrahydrofuran / 0.33 h / 0 °C 1.2: 60 percent / Pd2(dba)3; dppf / tetrahydrofuran / 13 h / 62 - 66 °C 2.1: 38 percent / I2 / acetonitrile / 3 h 3.1: 45 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 30 h / 60 - 63 °C View Scheme

1: ethynyl-magnesium bromide With zinc(II) chloride in tetrahydrofuran T=0°C; 0.333333 h; 2: methyl 2-(perfluoro-1-butanesulfonyloxy)benzoate With 1,1'-bis-(diphenylphosphino)ferrocene; tris(dibenzylideneacetone)dipalladium (0) in tetrahydrofuran T=62 - 66°C; 13 h;

potassium phosphate; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; tris-(dibenzylideneacetone)dipalladium(0) in toluene T=105°C; 14 h;

1.1: 75 percent / Et3N / Pd(PPh3)4; CuI / dimethylformamide / 24 h / 20 °C 2.1: LiOH / H2O; methanol / 18 h / 5 °C 2.2: 94 percent / H2SO4 / H2O / 0 °C View Scheme