1.1: pyridinium p-toluenesulfonate / dichloromethane / 0.5 h / 25 °C / Inert atmosphere 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 3.1: (R,R)-Co-salen; acetic acid / water; toluene / 20 °C / Cooling with ice 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere 5.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 4 h / 0 - 25 °C / Inert atmosphere 6.1: pyridinium p-toluenesulfonate / ethanol / 1 h / 60 °C 7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere 8.1: magnesium / tetrahydrofuran / 0.5 h / 20 - 25 °C / Inert atmosphere 8.2: 1 h / Inert atmosphere 9.1: pyridinium p-toluenesulfonate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere 11.1: triphenylphosphine; diethylazodicarboxylate / diethyl ether; benzene / 14 h / 20 °C 12.1: pyridinium p-toluenesulfonate / ethanol / 1 h / 60 °C 13.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / toluene / 23 h / 80 °C / Inert atmosphere 14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 0.5 h / 20 °C / Inert atmosphere 15.1: aluminium(III) iodide; tetra-(n-butyl)ammonium iodide / benzene / 10 °C View Scheme

1: PCC 2: CH2Cl2 / Ambient temperature 3: DIBAL View Scheme

o-nitrobenzenesulfonyl hydrazide; triphenylphosphine; diethylazodicarboxylate in toluene 1.) -30 deg C, 2.) reflux;

1: triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / -30 °C 2: tetrahydrofuran / 0 °C 3: tetrahydrofuran / 23 °C View Scheme

triphenylphosphine; diethylazodicarboxylate in tetrahydrofuran T=23°C; 1.) -30 deg C, 2 h; 2.) 23 deg C; Rate constant;

Rh(acetylacetonate)(CO)2; 6-[bis(4-fluorophenyl)phosphanyl]-1H-pyridin-2-one; N-(5-bis(4-methoxyphenyl)phosphanylpyrrol-2-carbonyl)guanidine; hydrogen in toluene T=80°C; P=15001.5 Torr; 24 h; Inert atmosphereAutoclave; regioselective reaction;

Rh(acetylacetonate)(CO)2; N-(5-diphenylphosphanylpyrrole-2-carbonyl)guanidine; hydrogen; 6-DPPon in toluene T=80°C; P=15001.5 Torr; 72 h; Inert atmosphereAutoclave; regioselective reaction;

1: 76.6 percent / chromic acid / acetone; H2O / < 5 deg C 2: 1) KOH / 1) DMSO, RT, 5 min, 2) 18h View Scheme

tributyltin chloride; bis-triphenylphosphine-palladium(II) chloride in 1,4-dioxane 3 h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: PBr3, Py / 0 °C 2: NaOEt / ethanol / Heating 3: (i) (saponification), (ii) (decarboxylation) 4: aq. H2SO4 / Heating View Scheme