1: 1.) n-butyllithium / 1.) hexane, THF, -100 deg, 2 h, 2.) THF, 0 deg C, 2 h 2: 53 percent / ammonium cerium(IV) nitrate / methanol; H2O / 3 h / Ambient temperature 3: 81 percent / Et3N / tetrahydrofuran / 8 h / Ambient temperature 4: 48 percent / p-TsOH, conc. HCl / methanol; H2O / 96 h / Heating 5: 90 percent / LiAlH4 / tetrahydrofuran / 16 h / Heating 6: 68 percent / Na, liquid ammonia / tetrahydrofuran / 0.75 h / -78 °C View Scheme

trimethylsilyl bromide; boron trifluoride diethyl etherate; copper; zinc in acetonitrile T=20°C; 0.666667 h; Product distribution; Further Variations:Reagentstime;

trimethylsilyl bromide; boron trifluoride diethyl etherate; copper; zinc in acetonitrile T=20°C; 0.666667 h; Product distribution; Further Variations:Reagentstime;

trimethylsilyl bromide; boron trifluoride diethyl etherate; copper; zinc in acetonitrile T=20°C; 0.666667 h; Product distribution; Further Variations:Reagentstime;

trimethylsilyl bromide; boron trifluoride diethyl etherate; copper; zinc in acetonitrile T=20°C; 0.666667 h; Product distribution; Further Variations:Reagentstime;

1: LDA / tetrahydrofuran; hexane / -70 °C / 1.) 15 min, 2.) 30 min 2: 80 percent / CAN / H2O; acetonitrile / 0.5 h / 0 °C 3: 80 percent / K2CO3 / dioxane; H2O / 0.17 h / Ambient temperature 4: 1.) (CF3CO)2O, sym-collidine, 2.) K2CO3, NaBH4 / 1.) MeCN, 0 deg C, 5 min, 2.) H2O, 0 deg C to room temperature, 15 min 5: 80 percent / H2 / Pd(OH)2/C / methanol / 0.25 h View Scheme

1: 100 percent / imidazole / dimethylformamide / 12 h / 20 °C 2: 99 percent / MeMgBr / tetrahydrofuran / -78 - -10 °C 3: 90 percent / CAN; H2O / acetonitrile / 0 °C 4: 90 percent / TBAF / tetrahydrofuran / 0.25 h / 0 °C View Scheme

1: N-benzylidene-p-methoxyaniline With neopentylmagnesium bromide; cobalt(II) dibromide; 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride in tetrahydrofuran T=0°C; Inert atmosphere; 2: N-benzylidene-p-methoxyaniline in tetrahydrofuran T=20°C; 12 h; Inert atmosphere; 3: 4-methoxy-benzaldehyde Further stages;

1: With 1-methyl-pyrrolidin-2-one; potassium carbonate; triphenylphosphine; [Ru(II)(η6-benzene)(μ-Cl)Cl]2 T=120°C; 20 h; 2: Further stages.;

1: triphenylphosphine; potassium carbonate; N-methylpyrrolidinone / [RuCl2(η6-C6H6)]2 / 20 h / 120 °C View Scheme