[Rh(OH)(cycloocta-1,5-diene)]2 in tetrahydrofuran T=35°C; 6 h;

chloro-trimethyl-silane T=-78 - 10°C; 5 h;

1: para-iodobenzonitrile With iso-propylmagnesium bromide in tetrahydrofuran T=-40°C; Metallation; 1 h; 2: cyclohexenon With chloro-trimethyl-silane; copper(l) iodide; lithium chloride in tetrahydrofuran Conjugate addition; 1 h;

1.1: i-PrMgBr / tetrahydrofuran / 10 h / -20 °C 1.2: 87 percent / tetrahydrofuran / 20 °C 2.1: 93 percent / [Rh(OH)(cod)]2 / tetrahydrofuran / 6 h / 35 °C View Scheme

1: para-bromobenzonitrile With diisobutyl-aluminum chloride in tetrahydrofuran T=-78°C; Inert atmosphereSchlenk technique; 2: With n-butyllithium in tetrahydrofuran; hexane T=-78 - 20°C; Inert atmosphereSchlenk technique; 3: cyclohexenon With chloro-trimethyl-silane; CuCN*2LiCl in tetrahydrofuran; hexane T=-40 - 25°C; Inert atmosphere;

1,4-diaza-bicyclo[2.2.2]octane; azacycloheptane; N,N'-dimethyl-N,N'-propyleneurea; [iridium(III)(2-phenylpyridine)3]; acetic acid in water T=23°C; Irradiation;

Pd(OPiv)2; silver trifluoroacetate; tri-iso-propyl phosphine in 1,4-dioxane T=80°C; Buchwald-Hartwig Coupling; 24 h; Schlenk techniqueGloveboxInert atmosphereSealed tube;

chloroform; palladium diacetate; caesium carbonate; triphenylphosphine in toluene T=80°C; 24 h; Inert atmosphere;