Multi-step reaction with 10 steps
1.1: lithium chloride; lithium diisopropyl amide / tetrahydrofuran / 1.5 h / -78 - 0 °C / Inert atmosphere
1.2: 20 °C / Inert atmosphere
2.1: tetra(n-butyl)ammonium hydroxide / tert-butyl alcohol; water / 36 h / 20 - 100 °C / Inert atmosphere
2.2: pH <= 1 / Inert atmosphere
3.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
4.1: tetrahydrofuran / 20.5 h / 20 °C / Inert atmosphere
5.1: S-alpine borane / tetrahydrofuran / 11 h / 20 °C / Inert atmosphere
6.1: triethylamine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere
7.1: N,N,N,N,N,N-hexamethylphosphoric triamide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; indium iodide / tetrahydrofuran / 8 h / 0 °C / Inert atmosphere
8.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
9.1: potassium carbonate / ethanol / 2 h / 20 °C / Inert atmosphere
10.1: 4-nitro-benzoic acid; [1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-2-(3H)-ylidene]gold(I)chloride; silver hexafluoroantimonate / dichloromethane / 0.08 h / 20 °C / Inert atmosphere
With
N,N,N,N,N,N-hexamethylphosphoric triamide; silver hexafluoroantimonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; indium iodide; di-isopropyl azodicarboxylate; [1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-2-(3H)-ylidene]gold(I)chloride; S-alpine borane; tetra(n-butyl)ammonium hydroxide; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; 4-nitro-benzoic acid;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/anie.201309449