1: 99 percent / aluminum chloride / 0 deg C, 1 h then 80 deg C, 2 h 2: 58 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 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: 58 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 4: 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: 99 percent / aluminum chloride / 0 deg C, 1 h then 80 deg C, 2 h 2: 58 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

sodium lauryl sulfate; sodium hydrogencarbonate; butan-1-ol; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; water Suzuki cross-coupling reaction; 7 h; Heating; Product distribution; Further Variations:CatalystsSolventsReagentstime;

1: 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 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

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;