1: 2-iodo aniline With methyllithium in tetrahydrofuran; diethyl ether T=-78°C; 0.5 h; Inert atmosphere; 2: 4-bromo-but-1-ene in tetrahydrofuran; diethyl ether T=-78°C; 0.166667 h; Inert atmosphere;

1.1: pyridine / tetrahydrofuran / 16 h / 20 °C 2.1: potassium hydroxide / dimethyl sulfoxide / 1 h / 20 °C 2.2: 3 h / 20 °C 3.1: potassium hydroxide / 2-methoxy-ethanol / 24 h / |Reflux View Scheme

tetrabutyl-ammonium chloride; sodium carbonate; palladium diacetate in N,N-dimethyl-formamide T=25°C; 24 h; Yield given;

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: 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; tris-(o-tolyl)phosphine / toluene / 8 h / 110 °C / |Sealed tube View Scheme

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; caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / 110 °C / |Sealed tube View Scheme

caesium carbonate; tris(dibenzylideneacetone)dipalladium (0); 1,3-bis(2,6-diisopropylphenyl)imidazolinium in dimethyl amine T=140°C; intramolecular Heck reaction; Title compound not separated from byproducts;

caesium carbonate; tris(dibenzylideneacetone)dipalladium (0); 1,3-bis(2,6-diisopropylphenyl)imidazolinium in dimethyl amine T=140°C; intramolecular Heck reaction; Title compound not separated from byproducts;