1.1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / ethylene glycol dimethyl ether; water / 12 h / 60 °C / |Inert atmosphere 2.1: dimethylsulfide borane complex / tetrahydrofuran / 24 h / 0 - 20 °C 2.2: 16 h / 20 °C 3.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 48 h / 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran; water / 5 h / 0 - 45 °C 4.2: 0 - 20 °C 5.1: palladium 10 on activated carbon; hydrogen / methanol / 6 h / 22502.3 Torr View Scheme

1.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / ethylene glycol dimethyl ether; water / 3 h / Reflux 2.1: borane-THF / tetrahydrofuran / 0 °C 2.2: 4 h / 0 °C 3.1: manganese(IV) oxide / chloroform / 48 h / Reflux 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 70 °C 4.2: 0 - 20 °C View Scheme