1: 3,4,5-trimethoxyphenylboronic acid With [Rh(1,5-cyclooctadiene)(NCCH3)2]BF4; (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl in 1,4-dioxane 0.5 h; 2: 6-methylcoumarin With triethylamine in 1,4-dioxane T=75°C; 0.75 h;

1: With sodium hydroxide; hydrogen; [RhCl(η2:η2-cycloocta-1,5-diene)]2 in methanol T=50°C; P=9000.9 Torr; 24 h; 2: With toluene-4-sulfonic acid in toluene 4 h; Heating; Further stages.;

sodium hydroxide; hydrogen; [RhCl(η2:η2-cycloocta-1,5-diene)]2 in methanol T=50°C; P=9000.9 Torr; 24 h; Title compound not separated from byproducts.;

toluene-4-sulfonic acid in toluene 4 h; Heating / reflux;

1.1: triphenylphosphine; lithium hydroxide hydrate; lithium chloride / water / |Reflux 2.1: calcium carbonate; palladium diacetate / methanol / 4 h / 60 °C 2.2: 20 °C 3.1: (R)-(S)-Cy2PF-PCy2; copper diacetate; DEMS / tetrahydrofuran; toluene; tert-butyl alcohol / 3 h / 20 °C / |Inert atmosphere 4.1: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / |Inert atmosphere View Scheme

1.1: calcium carbonate; palladium diacetate / methanol / 4 h / 60 °C 1.2: 20 °C 2.1: (R)-(S)-Cy2PF-PCy2; copper diacetate; DEMS / tetrahydrofuran; toluene; tert-butyl alcohol / 3 h / 20 °C / |Inert atmosphere 3.1: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / |Inert atmosphere View Scheme

1: (R)-(S)-Cy2PF-PCy2; copper diacetate; DEMS / tetrahydrofuran; toluene; tert-butyl alcohol / 3 h / 20 °C / |Inert atmosphere 2: pyridinium chlorochromate / dichloromethane / 3 h / 20 °C / |Inert atmosphere View Scheme

diisobutylaluminium hydride in toluene T=-25°C; 5 h;