palladium diacetate; potassium carbonate in water; acetone T=40°C; 72 h; Inert atmosphereReflux;

1: 78 percent / aluminum chloride / 0 deg C, 1 h then 80 deg C, 2 h 2: 80 percent / hydrazine hydrate, potassium hydroxide / bis-(2-hydroxy-ethyl) ether / 130 deg C, 2 h then 200 deg C, 2 h 3: 1.) butyl-lithium; 2.) tri-isopropyl borate; 3.) aq. sodium carbonate / 3.) tetrakis(triphenylphosphine)palladium(o) / 1.) THF/hexane, -78 deg C, 2.5 h; 2.) THF/hexane, rt.; 3.) ethanol/benzene, 23 h, reflux View Scheme

1: 80 percent / hydrazine hydrate, potassium hydroxide / bis-(2-hydroxy-ethyl) ether / 130 deg C, 2 h then 200 deg C, 2 h 2: 1.) butyl-lithium; 2.) tri-isopropyl borate; 3.) aq. sodium carbonate / 3.) tetrakis(triphenylphosphine)palladium(o) / 1.) THF/hexane, -78 deg C, 2.5 h; 2.) THF/hexane, rt.; 3.) ethanol/benzene, 23 h, reflux View Scheme

1: 78 percent / aluminum chloride / 0 deg C, 1 h then 80 deg C, 2 h 2: 80 percent / hydrazine hydrate, potassium hydroxide / bis-(2-hydroxy-ethyl) ether / 130 deg C, 2 h then 200 deg C, 2 h 3: 1.) butyl-lithium; 2.) tri-isopropyl borate; 3.) aq. sodium carbonate / 3.) tetrakis(triphenylphosphine)palladium(o) / 1.) THF/hexane, -78 deg C, 2.5 h; 2.) THF/hexane, rt.; 3.) ethanol/benzene, 23 h, reflux View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 - -70 °C / |Inert atmosphere 1.2: -70 - 20 °C / |Inert atmosphere 2.1: potassium carbonate; palladium diacetate / acetone; water / 72 h / 40 °C / |Inert atmosphere; |Reflux View Scheme

n-butyllithium; tri-isopropoxy-borane; sodium carbonate; tetrakis(triphenylphosphine) palladium(0) 1.) THF/hexane, -78 deg C, 2.5 h; 2.) THF/hexane, rt.; 3.) ethanol/benzene, 23 h, reflux; Yield given. Multistep reaction;

1: With potassium carbonate in water; acetone Suzuki-Miyaura Coupling; 0.333333 h; Inert atmosphereReflux; 2: With palladium diacetate in water; acetone Suzuki-Miyaura Coupling; 6 h; Inert atmosphereReflux;

n-butyllithium; tri-isopropoxy-borane; sodium carbonate; tetrakis(triphenylphosphine) palladium(0) 1.) THF/hexane, -78 deg C, 2.5 h; 2.) THF/hexane, rt.; 3.) ethanol/benzene, 23 h, reflux; Yield given. Multistep reaction;

n-butyllithium; tri-isopropoxy-borane; sodium carbonate; tetrakis(triphenylphosphine) palladium(0) 1.) THF/hexane, -78 deg C, 2.5 h; 2.) THF/hexane, rt.; 3.) ethanol/benzene, 23 h, reflux; Yield given. Multistep reaction;