1.1: copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 2.1: 167.9 mg / aq. HCl / 2 h / 50 °C 3.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 3.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C View Scheme

1: copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 2: 167.9 mg / aq. HCl / 2 h / 50 °C View Scheme

1: 1.) NaH, 2.) Cu / 1.) DMF, RT, 2.) DMF, 150 deg C, 4 h 2: 90 percent / 1 N aq. HCl / 2 h / Ambient temperature View Scheme

1: (i) Mg, THF, (ii) /BRN= 1900390/, (iii) aq. H2SO4 2: NaOAc / 10 h / 150 - 160 °C / Heating 3: (i) SOCl2, (ii) /BRN= 1718733/ 4: Br2 / CHCl3 / 10 h / Heating 5: KOH / ethanol / 24 h / Heating 6: Cu / quinoline / 1 h / 90 °C View Scheme

1.1: copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 2.1: 167.9 mg / aq. HCl / 2 h / 50 °C 3.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 3.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C 4.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 5.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 5.2: 55 percent / acetic acid / toluene; H2O 6.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme

(i) Mg, THF, (ii) /BRN= 1900390/, (iii) aq. H2SO4; Multistep reaction;

1: With copper(l) iodide; triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride Sonogashira reaction; 20 h; Heating; 2: With sodium hydride in toluene 6 h; Heating;

1: Li 2: Acid hydrolysis View Scheme

1.1: Mg / tetrahydrofuran / 1 h / Heating 1.2: tetrahydrofuran / 2 h / Heating 2.1: aq. HCl; acetone / 0.5 h / 20 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.42 h / -78 °C / Inert atmosphere 1.2: 20 h / -78 - 20 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / tetrahydrofuran; water / 4 h / 20 °C / Inert atmosphere View Scheme