dichloro(cycloocta-1,5-diene)palladium(II); N,N-dicyclohexylmethylamine; potassium formiate; tetra-(n-butyl)ammonium iodide; PCy3∙HBF4; bis(dibenzylideneacetone)-palladium(0); [(t-Bu)3PH]BF4 T=100°C; 18 h; Sealed tubeGloveboxInert atmosphere; Reagent/catalystSolvent;

dichloro(cycloocta-1,5-diene)palladium(II); t-Bu Brett Phos; N,N-dicyclohexylmethylamine; COgen; bis(dibenzylideneacetone)-palladium(0); [(t-Bu)3PH]BF4 in 1,4-dioxane T=80°C; 18 h; Inert atmosphere; Reagent/catalyst;

dichloro(cycloocta-1,5-diene)palladium(II); N,N-dicyclohexylmethylamine; 1,5-bis-(diphenylphosphino)-pentane; COgen; bis(dibenzylideneacetone)-palladium(0); [(t-Bu)3PH]BF4 in 1,4-dioxane T=80°C; 18 h; Inert atmosphere; Reagent/catalyst;

1: 81 percent / Et3N; LiBr / tetrahydrofuran / 4 h / 20 °C 2: 95 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / 0 °C 3: (-)-diisopropyl tartrate; t-BuOOH; 4 Angstroem molecular sieves / Ti(OPr-i)4 / CH2Cl2; 2,2,4-trimethyl-pentane / 2 h / -25 °C 4: 64 percent / aq. NaOH / 2.5 h / 70 °C 5: 100 percent / Et3N / CH2Cl2 / 12 h / 20 °C 6: 71 percent / NaI / butan-2-one / 4 h / Heating 7: 69 percent / Bu3SnH; AIBN / toluene / 2 h / 80 °C 8: t-BuLi / hexane; tetrahydrofuran / 2 h / 20 °C 9: Na(Hg) / methanol; H2O / 12 h View Scheme

N-methylamine hydrochloride in ethanol T=150°C; 20 h; Product distribution;