1.1: sodium tetrahydroborate; silica gel / methanol; dichloromethane / 0.58 h 2.1: acetonitrile / 8 h / 100 °C 2.2: 12 h / 90 °C View Scheme

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

1.1: 73 percent / (S)-BINOL; Ti(OiPr)4; 4 Angstroem MS / CH2Cl2 / 70 h / -20 °C 2.1: 87 percent / imidazole / CH2Cl2 / 4 h / 0 °C 3.1: 85 percent / Mg / methanol / 3 h / 20 °C 4.1: 73 percent / K2CO3 / acetone / 4 h / Heating 5.1: O3 / CH2Cl2 / 1 h / -78 °C 5.2: TPP / CH2Cl2 6.1: CH2Cl2 / 2 h / 20 °C 7.1: 81 percent / Mg / 3 h / 20 °C 8.1: 76 percent / LAH / tetrahydrofuran / 3 h / 0 - 20 °C 9.1: 80 percent / IBX / dimethylsulfoxide / 4 h / 20 °C 10.1: 81 percent / Ba(OH)2*8H2O / tetrahydrofuran; H2O / 5 h / 20 °C 11.1: 80 percent / HF*Py / tetrahydrofuran / 4 h / Heating 12.1: 70 percent / H2; HCl / Pd/C / ethanol; ethyl acetate; H2O / 10 h View Scheme

1,1'-bis-(diphenylphosphino)ferrocene; (9-phenanthrenyl)Ni(II)(PPh3)2Cl; potassium carbonate in toluene T=110°C; Suzuki Coupling; 20 h; Inert atmosphere;

triethylamine; palladium diacetate in ethanol T=80°C; Suzuki-Miyaura cross-coupling;

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

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

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: Et3N / CH2Cl2 / 1 h / 0 °C 5: 279.8 mg / NaI / 1,2-dimethoxy-ethane / 12 h / Heating 6: 100 percent / sym-collidine / CH2Cl2 / 0.25 h / -78 °C 7: 99 percent / H2 / Rh-Al2O3 / tetrahydrofuran / 12 h / 760.05 Torr 8: 60 percent / Na(Hg) / methanol; H2O / 0.75 h 9: 75 percent / Et3N / CH2Cl2 / 0.17 h / -78 °C 10: 100 percent / H2; Et3N / Pd/C / ethyl acetate / 3 h / 760.05 Torr 11: Bu4NF / tetrahydrofuran / 12 h View Scheme

triethylamine in dichloromethane T=0 - 20°C; 1 h;

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 in acetonitrile T=80°C; 18 h; Sealed tubeGloveboxInert atmosphere; Reagent/catalystSolvent;