Multi-step reaction with 10 steps
1.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 °C
1.2: 20 °C
2.1: water; ammonium cerium (IV) nitrate / acetonitrile / 1 h / 70 °C
3.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C
3.2: 20 °C
4.1: potassium acetate / 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere
5.1: potassium phosphate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 90 °C / Inert atmosphere
6.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 45 °C / Inert atmosphere; sealed tube
7.1: N-iodo-succinimide / acetonitrile / 1 h / 20 °C
8.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 16 h / 90 °C
9.1: N-Bromosuccinimide / acetonitrile / 0.5 h / 20 °C
10.1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere
With
potassium phosphate; N-Bromosuccinimide; N-iodo-succinimide; ammonium cerium (IV) nitrate; water; hydrogen; potassium acetate; lithium diisopropyl amide;
1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; water; ethyl acetate; acetonitrile;