1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / |Inert atmosphere 1.2: 12 h / -78 - 23 °C / |Inert atmosphere 2.1: [MeCNAu((1,1′-biphenyl-2-yl)-di-tert-butylphosphine)]+SbF6− / 1,2-dichloro-ethane / 3 h / 120 °C / |Sealed tube; |Inert atmosphere View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethanol; water; toluene T=90°C; 3.5 h;

tetrakis(triphenylphosphine) palladium(0); potassium carbonate in N,N-dimethyl-formamide T=110°C; Suzuki coupling; 14 h;

Aliquatreg; 336; sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in water; toluene T=90°C; Suzuki-Miyaura coupling; 5 h;

tetrakis(triphenylphosphine) palladium(0); potassium carbonate in toluene T=85°C; Suzuki coupling; 24 h; Inert atmosphere;

1: 31.38 g / toluene / 2 h / Heating 2: 70 percent / aliquate 336; Na2CO3 / tetrakis(triphenylphosphine)palladium(0) / toluene; H2O / 5 h / 90 °C View Scheme

1: triisopropyl borate; n-butyllithium / toluene; tetrahydrofuran; hexane / 2.08 h / -70 - 20 °C 2: aq. HCl / toluene; tetrahydrofuran; hexane / 0.5 h / 20 °C 3: 31.38 g / toluene / 2 h / Heating 4: 70 percent / aliquate 336; Na2CO3 / tetrakis(triphenylphosphine)palladium(0) / toluene; H2O / 5 h / 90 °C View Scheme

1: (i), (ii) H3PO4, H2SO4 2: S / 260 - 280 °C View Scheme

1: (i), (ii) H3PO4, H2SO4 2: S / 260 - 280 °C View Scheme