(tetraoctylammonium)AuCl4; water in dichloromethane T=20°C; 24 h;

caesium carbonate; palladium diacetate in acetonitrile T=100°C; 24 h;

1: 3-phenyl-3-hydroxypropene With α-cyclohexylcyclohexanemethanamine; tetrabutylammomium bromide in N,N-dimethyl acetamide; water T=20°C; Heck reaction; 0.25 h; 2: 2-iodophenol With 4'-hydroxyacetophenone oxime palladacycle catalyst in N,N-dimethyl acetamide; water T=120°C; Heck reaction; 4 h; Further stages. Title compound not separated from byproducts.;

1: 3-phenyl-3-hydroxypropene With α-cyclohexylcyclohexanemethanamine; tetrabutylammomium bromide in water T=20°C; Heck reaction; 0.25 h; 2: 2-iodophenol With 4'-hydroxyacetophenone oxime palladacycle catalyst in water T=120°C; Heck reaction; 14 h; Further stages. Further byproducts. Title compound not separated from byproducts.;

1: 3-phenyl-3-hydroxypropene With α-cyclohexylcyclohexanemethanamine; tetrabutylammomium bromide in N,N-dimethyl acetamide T=20°C; Heck reaction; 0.25 h; 2: ortho-bromo-phenol With 4'-hydroxyacetophenone oxime palladacycle catalyst in N,N-dimethyl acetamide T=120°C; Heck reaction; 14 h; Further stages.;

1: 100 percent Spectr. / tetrahydrofuran / 2 h / 0 °C 2: 61 percent / Cs2CO3 / Pd(OAc)2 / acetonitrile / 24 h / 100 °C View Scheme

boron trifluoride diethyl etherate in 1,2-dichloro-ethane T=70°C; 0.5 h;

1: 63 mg / tri-n-butyltin hydride / benzene / 0.5 h / Heating; further reagents 2: 0.76 g / aluminium chloride, lithium aluminium hydride / tetrahydrofuran; diethyl ether / 0.33 h / 0 °C 3: 900 mg / aluminium chloride / 96 h 4: aq. hydrochloric acid / ethanol / 3.5 h View Scheme

1: sodium hydroxide / water; ethanol 2: sodium tetrahydroborate / isopropyl alcohol 3: (tetraoctylammonium)AuCl4; water / dichloromethane / 24 h / 20 °C View Scheme

1: sodium tetrahydroborate / isopropyl alcohol 2: (tetraoctylammonium)AuCl4; water / dichloromethane / 24 h / 20 °C View Scheme