palladium diacetate; tetrabutyl ammonium fluoride; triphenylphosphine in tetrahydrofuran; N,N-dimethyl-formamide T=90°C;

in chlorobenzene T=132°C;

1.1: n-BuLi / tetrahydrofuran; diethyl ether; hexane / 20 h / 25 °C 1.2: 62 percent / tetrahydrofuran; diethyl ether; hexane / 4 h / 20 °C 2.1: 86 percent / Pd(OAc)2; PPh3; TBAF / dimethylformamide; tetrahydrofuran / 90 °C View Scheme

1.1: 96 percent / Na2CO3 / H2O; CH2Cl2 / 1 h / Heating 2.1: n-BuLi / tetrahydrofuran; diethyl ether; hexane / 20 h / 25 °C 2.2: 62 percent / tetrahydrofuran; diethyl ether; hexane / 4 h / 20 °C 3.1: 86 percent / Pd(OAc)2; PPh3; TBAF / dimethylformamide; tetrahydrofuran / 90 °C View Scheme

1.1: 96 percent / Na2CO3 / H2O; CH2Cl2 / 1 h / Heating 2.1: n-BuLi / tetrahydrofuran; diethyl ether; hexane / 20 h / 25 °C 2.2: 62 percent / tetrahydrofuran; diethyl ether; hexane / 4 h / 20 °C 3.1: 86 percent / Pd(OAc)2; PPh3; TBAF / dimethylformamide; tetrahydrofuran / 90 °C View Scheme

palladium diacetate; silver carbonate T=125°C; 16 h;

[bis(acetoxy)iodo]benzene; copper(II) bis(trifluoromethanesulfonate); trifluoroacetic acid in 1,2-dichloro-ethane T=50°C; 0.25 h;