piperidine; copper(l) iodide; [Pd(PPh3)2(OAc)2] in N,N-dimethyl-formamide T=60°C; 5 h;

1: NaOH / ethanol / 8 h / Heating 2: 1.00 g / imidazole / CH2Cl2 / 2 h / 20 °C 3: TBAF*3H2O / PdCl2(PPh3)2 / 60 °C View Scheme

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C 1.2: 88 percent / I2 / tetrahydrofuran; hexane / -78 - 20 °C 2.1: NaOH / ethanol / 8 h / Heating 3.1: 1.00 g / imidazole / CH2Cl2 / 2 h / 20 °C 4.1: TBAF*3H2O / PdCl2(PPh3)2 / 60 °C View Scheme

1: 1.00 g / imidazole / CH2Cl2 / 2 h / 20 °C 2: TBAF*3H2O / PdCl2(PPh3)2 / 60 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C 1.2: 87 percent / hexane; tetrahydrofuran / 36 h / Heating 2.1: s-BuLi; TMEDA / cyclohexane; hexane; tetrahydrofuran / 2 h / -78 °C 2.2: 86 percent / iodine / tetrahydrofuran; hexane; cyclohexane / -78 - 20 °C 3.1: 88 percent / NaOH / ethanol / Heating 4.1: 61 percent / piperidine; CuI / Pd(OAc)2(PPh3)2 / dimethylformamide / 5 h / 60 °C View Scheme

tetrabutyl ammonium fluoride; bis-triphenylphosphine-palladium(II) chloride T=60°C;

1: anhydrous dichlorophenol With dichloro bis(acetonitrile) palladium(II); C31H36O2*BF4(1-)*H(1+); lithium tert-butylate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl in toluene T=20°C; Sonogashira Cross-Coupling; 0.25 h; Inert atmosphere; 2: phenylacetylene in toluene 0.75 h; Inert atmosphereReflux; 3: in water; toluene 2 h; Inert atmosphereReflux;