1.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: potassium carbonate / tetrahydrofuran; methanol / 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere 4.1: RuCl2(tricyclohexylphosphine)2(benzylidene); ethene / 20 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere 6.1: MgBr2*Et2O; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere 6.2: 6 h / 20 °C / Inert atmosphere 7.1: diisobutylaluminium hydride / dichloromethane / 2.25 h / -78 °C / Inert atmosphere 8.1: benzene / 24 h / Inert atmosphere; Reflux 9.1: (tricyclohexylphosphine)(1,5-cyclooctadiene)pyridineiridium(I) hexafluorophosphate; hydrogen / dichloromethane / 2.25 h / 0 - 20 °C / Inert atmosphere 10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2.5 h / 20 °C / Inert atmosphere 11.1: pyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 12.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 12.2: 15.75 h / 0 - 20 °C / Inert atmosphere 13.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 24 h / 20 °C / Inert atmosphere View Scheme

pyridine in dichloromethane T=0°C; Yield given;

1: Py 2: (i) Li, CuI, Et2O, (ii) /BRN= 2361172/ 3: KF / dimethylformamide; H2O View Scheme

1: Py 2: (i) Li, CuI, Et2O, (ii) /BRN= 2361172/ 3: KF / dimethylformamide; H2O 4: (i) nBuLi, (ii) /BRN= 1922354/, HMPT View Scheme