potassium tert-butylate in tetrahydrofuran Heating;

potassium phosphate; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) in N,N-dimethyl-formamide T=80°C; Suzuki-Miyaura coupling; 10 h; Inert atmosphere;

palladium diacetate; potassium carbonate in methanol Suzuki-Miyaura cross-coupling; 12 h; Heating;

1.1: 100 percent / NaH / various solvent(s); tetrahydrofuran / 20 °C 2.1: 84 percent / tert-butyllithium / hexane; tetrahydrofuran / 3 h / -78 °C 3.1: s-butyllithium; TMEDA / tetrahydrofuran; hexane / -78 °C 3.2: B(O-iPr)3 / tetrahydrofuran; hexane / -78 - 20 °C 3.3: 60 percent / hexane; ethyl acetate; tetrahydrofuran 4.1: 94 percent / Pd(PPh3)4; K3PO4 / dimethylformamide / 17 h / 80 °C 5.1: 71 percent / potassium tert-butylate / tetrahydrofuran / Heating View Scheme

1.1: 84 percent / tert-butyllithium / hexane; tetrahydrofuran / 3 h / -78 °C 2.1: s-butyllithium; TMEDA / tetrahydrofuran; hexane / -78 °C 2.2: B(O-iPr)3 / tetrahydrofuran; hexane / -78 - 20 °C 2.3: 60 percent / hexane; ethyl acetate; tetrahydrofuran 3.1: 94 percent / Pd(PPh3)4; K3PO4 / dimethylformamide / 17 h / 80 °C 4.1: 71 percent / potassium tert-butylate / tetrahydrofuran / Heating View Scheme

1.1: s-butyllithium; TMEDA / tetrahydrofuran; hexane / -78 °C 1.2: B(O-iPr)3 / tetrahydrofuran; hexane / -78 - 20 °C 1.3: 60 percent / hexane; ethyl acetate; tetrahydrofuran 2.1: 94 percent / Pd(PPh3)4; K3PO4 / dimethylformamide / 17 h / 80 °C 3.1: 71 percent / potassium tert-butylate / tetrahydrofuran / Heating View Scheme

1: 94 percent / Pd(PPh3)4; K3PO4 / dimethylformamide / 17 h / 80 °C 2: 71 percent / potassium tert-butylate / tetrahydrofuran / Heating View Scheme

1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 5 h / 80 °C / |Inert atmosphere 2: tetrahydrofuran / 0.25 h / 0 °C / |Inert atmosphere View Scheme

1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 5 h / 80 °C / |Inert atmosphere 2: tetrahydrofuran / 0.25 h / 0 °C / |Inert atmosphere View Scheme

in tetrahydrofuran T=0°C; 0.25 h; Inert atmosphere; Overall yield = 66 percent;