sodium tetrahydroborate; trifluoroacetic acid in dichloromethane T=0°C; 0.5 h;

1: Merrifield resin-CH2O(CH2)4S-CH2C6H3-3,4-OCH2O- With triethyloxonium tetra-fluoroborate in dichloromethane T=20°C; Solid phase reaction; Alkylation the sulfur atom; 8 h; 2: 3,4,5-trimethoxyphenylboronic acid With potassium carbonate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) in tetrahydrofuran T=60°C; Arylation; Cleavage from the resin; 14 h;

dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; potassium carbonate in tetrahydrofuran; water T=80°C; Suzuki-Miyaura Coupling; 48 h; Inert atmosphereSealed tube;

bis(1,5-cyclooctadiene)nickel (0); cesium fluoride; diphenylcyclohexyl phosphine in 1,4-dioxane T=40°C; 24 h; Inert atmosphereGlovebox;

[Pd(CH3CN)4]*[BF4]2; potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether in N,N-dimethyl-formamide T=60°C; 6 h; Inert atmosphere;

1: 80 percent / tetrahydrofuran / 0.5 h / Ambient temperature 2: 90 percent / CF3COOH, NaBH4 / CH2Cl2 / 0.5 h / 0 °C View Scheme

1: 80 percent / tetrahydrofuran / 0.5 h / Ambient temperature 2: 90 percent / CF3COOH, NaBH4 / CH2Cl2 / 0.5 h / 0 °C View Scheme

1: diethyl ether / 0.25 h / 0 °C 2: bis(1,5-cyclooctadiene)nickel (0); diphenylcyclohexyl phosphine; cesium fluoride / 1,4-dioxane / 24 h / 40 °C / |Inert atmosphere; |Glovebox View Scheme

1.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 0.17 h / 0 °C / |Inert atmosphere 1.2: 0.5 h / 20 °C / |Inert atmosphere 2.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 0.17 h / 0 °C / |Inert atmosphere 2.2: 2 h / 20 °C / |Inert atmosphere 3.1: bis[2-(diphenylphosphino)phenyl] ether; [Pd(CH3CN)4]*[BF4]2; potassium carbonate / N,N-dimethyl-formamide / 6 h / 60 °C / |Inert atmosphere View Scheme

1.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 0.17 h / 0 °C / |Inert atmosphere 1.2: 2 h / 20 °C / |Inert atmosphere 2.1: bis[2-(diphenylphosphino)phenyl] ether; [Pd(CH3CN)4]*[BF4]2; potassium carbonate / N,N-dimethyl-formamide / 6 h / 60 °C / |Inert atmosphere View Scheme