Multi-step reaction with 11 steps
1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C
1.2: 0.33 h / -78 °C
1.3: 21 h / -78 - 20 °C
2.1: boron tribromide / dichloromethane / 6.5 h / -78 - -20 °C
3.1: calcium sulfate; scandium tris(trifluoromethanesulfonate) / 1,2-dichloro-ethane / 2.5 h / -30 - -10 °C / Inert atmosphere
4.1: calcium sulfate; scandium tris(trifluoromethanesulfonate) / 1,2-dichloro-ethane / 20 h / -30 - 28 °C / Inert atmosphere
5.1: tetra-(n-butyl)ammonium iodide; sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.67 h / 0 °C
5.2: 5 h / 0 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 - 0 °C
6.2: 2.5 h / -78 °C
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 3 h / 0 - 20 °C
8.1: potassium carbonate / methanol / 6 h / 0 - 20 °C
9.1: water; bis-[(trifluoroacetoxy)iodo]benzene / acetonitrile / 1 h / 0 °C / Darkness
10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / [D3]acetonitrile / 1 h / 0 °C
11.1: trimethylphosphane / dichloromethane; toluene / 4 h / 0 - 20 °C / Darkness
11.2: 2 h / 0 - 20 °C / pH 4
With
calcium sulfate; lithium aluminium tetrahydride; water; boron tribromide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; bis-[(trifluoroacetoxy)iodo]benzene; scandium tris(trifluoromethanesulfonate); lithium diisopropyl amide; trimethylphosphane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; dichloromethane; [D3]acetonitrile; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;
DOI:10.1002/anie.201308017