dichloro bis(acetonitrile) palladium(II) in N,N-dimethyl-formamide T=25°C; Stille cross-coupling reaction; 3 h;

1.1: NBS; AIBN / CCl4 2.1: aq. NaOH 3.1: 89 percent / Zn; AcOH 4.1: 79 percent / NBS; AIBN / CCl4 5.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 5.2: 70 percent / tetrahydrofuran; hexane / 1 h / -78 °C 6.1: 71 percent / DBU / tetrahydrofuran / 5 h / 20 °C View Scheme

1.1: 89 percent / Zn; AcOH 2.1: 79 percent / NBS; AIBN / CCl4 3.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 3.2: 70 percent / tetrahydrofuran; hexane / 1 h / -78 °C 4.1: 71 percent / DBU / tetrahydrofuran / 5 h / 20 °C View Scheme

1.1: 79 percent / NBS; AIBN / CCl4 2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 2.2: 70 percent / tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 71 percent / DBU / tetrahydrofuran / 5 h / 20 °C View Scheme

1.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 70 percent / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 71 percent / DBU / tetrahydrofuran / 5 h / 20 °C View Scheme

1.1: aq. NaOH 2.1: 89 percent / Zn; AcOH 3.1: 79 percent / NBS; AIBN / CCl4 4.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C 4.2: 70 percent / tetrahydrofuran; hexane / 1 h / -78 °C 5.1: 71 percent / DBU / tetrahydrofuran / 5 h / 20 °C View Scheme