ammonium hydroxide in water T=20 - 103°C; sealed tube; Product distribution / selectivity;

1.1: pyridine / dichloromethane / 15 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 3 °C 3.1: N-bromosuccinmide / dichloromethane / 10 - 20 °C 3.2: 2.5 h / 10 - 75 °C 4.1: ammonium hydroxide / water / 20 - 103 °C / sealed tube View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 3 °C 2.1: N-bromosuccinmide / dichloromethane / 10 - 20 °C 2.2: 2.5 h / 10 - 75 °C 3.1: ammonium hydroxide / water / 20 - 103 °C / sealed tube View Scheme

1: N-bromosuccinmide / N,N-dimethyl acetamide / 0.25 h / 20 °C 2: N,N-dimethyl acetamide / 20 - 60 °C 3: N,N-dimethyl acetamide / 60 - 80 °C 4: ammonia / methanol / 24 h / 90 °C / |Sealed tube View Scheme

1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 2: pyridine / dichloromethane / 20 °C 3: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C / |Cooling with ice 4: N-bromosuccinmide / N,N-dimethyl acetamide / 0.25 h / 20 °C 5: N,N-dimethyl acetamide / 20 - 60 °C 6: N,N-dimethyl acetamide / 60 - 80 °C 7: ammonia / methanol / 24 h / 90 °C / |Sealed tube View Scheme

1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; caesium carbonate / 90 °C / |Sealed tube; |Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: pyridine / dichloromethane / 20 °C 4: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C / |Cooling with ice 5: N-bromosuccinmide / N,N-dimethyl acetamide / 0.25 h / 20 °C 6: N,N-dimethyl acetamide / 20 - 60 °C 7: N,N-dimethyl acetamide / 60 - 80 °C 8: ammonia / methanol / 24 h / 90 °C / |Sealed tube View Scheme

1: sulfuric acid / 1 h / |Reflux 2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene; caesium carbonate / 90 °C / |Sealed tube; |Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4: pyridine / dichloromethane / 20 °C 5: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C / |Cooling with ice 6: N-bromosuccinmide / N,N-dimethyl acetamide / 0.25 h / 20 °C 7: N,N-dimethyl acetamide / 20 - 60 °C 8: N,N-dimethyl acetamide / 60 - 80 °C 9: ammonia / methanol / 24 h / 90 °C / |Sealed tube View Scheme

1.1: pyridine / dichloromethane / 15 - 25 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 3 °C 3.1: N-bromosuccinmide / dichloromethane / 10 - 20 °C 3.2: 2.5 h / 10 - 75 °C 4.1: ammonium hydroxide / water / 20 - 103 °C / sealed tube View Scheme

in water; acetonitrile T=20 - 60°C; Product distribution / selectivity;