tetraethyl ammonium [18]F-fluoride; TEAHCO3 in acetonitrile T=90°C; 0.166667 h; Product distribution / selectivity;

1.1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 65 °C 2.1: phosphorus tribromide / dichloromethane / 1 h / 25 °C 3.1: potassium tert-butylate / 60 °C 3.2: 16.5 h / 60 °C 4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 22 h / 20 °C 5.1: TEAHCO3; tetraethyl ammonium [18]F-fluoride / acetonitrile / 0.17 h / 90 °C View Scheme

1: di-isopropyl azodicarboxylate / triphenylphosphine / tetrahydrofuran / 20 h / 20 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 22 h / 20 °C 4: TEAHCO3; tetraethyl ammonium [18]F-fluoride / acetonitrile / 0.17 h / 90 °C View Scheme

1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -10 - 20 °C / Cooling with ice 2: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C 4: di-isopropyl azodicarboxylate / triphenylphosphine / tetrahydrofuran / 20 h / 20 °C 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 6: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 22 h / 20 °C 7: TEAHCO3; tetraethyl ammonium [18]F-fluoride / acetonitrile / 0.17 h / 90 °C View Scheme

1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C 3: di-isopropyl azodicarboxylate / triphenylphosphine / tetrahydrofuran / 20 h / 20 °C 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 5: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 22 h / 20 °C 6: TEAHCO3; tetraethyl ammonium [18]F-fluoride / acetonitrile / 0.17 h / 90 °C View Scheme

1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C 2: di-isopropyl azodicarboxylate / triphenylphosphine / tetrahydrofuran / 20 h / 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 4: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 22 h / 20 °C 5: TEAHCO3; tetraethyl ammonium [18]F-fluoride / acetonitrile / 0.17 h / 90 °C View Scheme

1: di-isopropyl azodicarboxylate / triphenylphosphine / tetrahydrofuran / 20 h / 20 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 22 h / 20 °C 4: TEAHCO3; tetraethyl ammonium [18]F-fluoride / acetonitrile / 0.17 h / 90 °C View Scheme

1.1: orthoformic acid triethyl ester / 0.58 h / 22 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran 3.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / toluene; water / 2.5 h / 39 °C 4.1: diisobutylaluminium hydride / dichloromethane / 1 h / -40 °C 4.2: 22 °C 5.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 22 h / 20 °C 6.1: TEAHCO3; tetraethyl ammonium [18]F-fluoride / acetonitrile / 0.17 h / 90 °C View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran 2.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / toluene; water / 2.5 h / 39 °C 3.1: diisobutylaluminium hydride / dichloromethane / 1 h / -40 °C 3.2: 22 °C 4.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 22 h / 20 °C 5.1: TEAHCO3; tetraethyl ammonium [18]F-fluoride / acetonitrile / 0.17 h / 90 °C View Scheme

1.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / toluene; water / 2.5 h / 39 °C 2.1: diisobutylaluminium hydride / dichloromethane / 1 h / -40 °C 2.2: 22 °C 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 22 h / 20 °C 4.1: TEAHCO3; tetraethyl ammonium [18]F-fluoride / acetonitrile / 0.17 h / 90 °C View Scheme