1: hydrazine hydrate; potassium hydroxide; triethylene glycol / 200 °C / Entfernen des entstehenden Wassers 2: cyanogen bromide / Erhitzen des erhaltenen 2,3,4,5-Tetrahydro-benz<b>azepin-1-carbonitrils mit konz. wss. Salzsaeure View Scheme

tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(di-tert-butylphosphino)ferrocene; caesium carbonate; triethylamine in toluene T=110°C; 24 h; Sealed tube; chemoselective reaction;

tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; triethylamine; tris-(o-tolyl)phosphine in toluene T=110°C; 8 h; Sealed tube; chemoselective reaction;

potassium tert-butylate; toluene Erwaermen des jeweils erhaltenen Reaktionsgemisches mit wss.Salzsaeure;

2: potassium tert-butylate; toluene / Erwaermen des jeweils erhaltenen Reaktionsgemisches mit wss.Salzsaeure View Scheme

3: potassium tert-butylate; toluene / Erwaermen des jeweils erhaltenen Reaktionsgemisches mit wss.Salzsaeure View Scheme

tetrakis(triphenylphosphine) palladium(0); caesium carbonate; triethylamine in toluene T=110°C; Sealed tube; chemoselective reaction;

1.1: potassium carbonate / acetonitrile / 65 h / 50 °C / |Sealed tube 2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran; water / 18 h / 0 - 20 °C / |Inert atmosphere 2.2: 3 h / 20 - 50 °C 3.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.25 h / -60 °C 3.2: 0.08 h 4.1: triethylamine; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 1,1'-bis-(di-tert-butylphosphino)ferrocene / toluene / 24 h / 110 °C / |Sealed tube View Scheme

1.1: methyllithium / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C / |Inert atmosphere 1.2: 0.17 h / -78 °C / |Inert atmosphere 2.1: potassium carbonate / acetonitrile / 65 h / 50 °C / |Sealed tube 3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran; water / 18 h / 0 - 20 °C / |Inert atmosphere 3.2: 3 h / 20 - 50 °C 4.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.25 h / -60 °C 4.2: 0.08 h 5.1: triethylamine; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 1,1'-bis-(di-tert-butylphosphino)ferrocene / toluene / 24 h / 110 °C / |Sealed tube View Scheme

1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran; water / 18 h / 0 - 20 °C / |Inert atmosphere 1.2: 3 h / 20 - 50 °C 2.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.25 h / -60 °C 2.2: 0.08 h 3.1: triethylamine; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 1,1'-bis-(di-tert-butylphosphino)ferrocene / toluene / 24 h / 110 °C / |Sealed tube View Scheme