1: palladium / Hydrogenation 2: aqueous HBr; glacial acetic acid View Scheme

1: With trifuran-2-yl-phosphane; tetra-(n-butyl)ammonium iodide; tris-(dibenzylideneacetone)dipalladium(0) in 1-methyl-pyrrolidin-2-one T=20°C; Negishi Coupling Reaction; 2: With ammonium chloride in 1-methyl-pyrrolidin-2-one; water

tetra-(n-butyl)ammonium iodide; tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane in 1-methyl-pyrrolidin-2-one T=20°C; Negishi Coupling Reaction;

sulfuric acid in acetic acid

1: (3-methoxyphenyl)-magnesium bromide With tris-(dibenzylideneacetone)dipalladium(0); pinacol phosphonate in tetrahydrofuran T=20°C; Kumada-Corriu cross-coupling reaction; 0.0833333 h; Inert atmosphere; 2: cyclohex-1-en-1-yl 4-methylbenzenesulfonate in tetrahydrofuran T=20°C; Kumada-Corriu cross-coupling reaction; 22 h; Inert atmosphere; chemoselective reaction;

diethyl ether Erhitzen des Reaktionsprodukts mit wss. H2SO4;

1,2-dimethoxy-benzene; Pd(F6-acac)2; 1,3-bis-(diphenylphosphino)propane; lithium carbonate T=120°C; Heck Reaction; 60 h; Inert atmosphere;

1: pyridine / dichloromethane / 5 h / 25 °C / |Inert atmosphere 2: Pd(F6-acac)2; 1,3-bis-(diphenylphosphino)propane; lithium carbonate; 1,2-dimethoxy-benzene / 60 h / 120 °C / |Inert atmosphere View Scheme

(i) Mg, Et2O, (ii) /BRN= 385735/, (iii) TsOH, benzene; Multistep reaction;

1: 2: Acidic conditions;