Multi-step reaction with 11 steps
1.1: 1H-imidazole; triphenylphosphine; iodine / dichloromethane; toluene / 1.75 h / 45 °C / Inert atmosphere
2.1: 1H-imidazole / dichloromethane / 4.5 h / 0 - 20 °C / Inert atmosphere
3.1: dmap / 1,2-dichloro-ethane / 1 h / 50 °C / Inert atmosphere; Sealed tube
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 12 h / 80 °C / Inert atmosphere
5.1: mercury(II) trifluoroacetate / water; acetone / 20 h / 20 °C / Inert atmosphere; Sealed tube
6.1: triethylamine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere
7.1: dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
8.1: titanium tetrachloride / toluene / 1.17 h / -78 °C / Inert atmosphere
8.2: 5 h / -78 - 5 °C / Inert atmosphere
9.1: 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide / acetonitrile / 3 h / 82 °C / Inert atmosphere
10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 3 h / 20 °C / Inert atmosphere
11.1: diethylzinc / toluene; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
11.2: 0.5 h / -78 - 0 °C / Inert atmosphere
11.3: 0.33 h / -78 - -20 °C / Inert atmosphere
With
1H-imidazole; dmap; iodine; diethylzinc; mercury(II) trifluoroacetate; titanium tetrachloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide;
In
tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; acetone; toluene; acetonitrile;
DOI:10.1021/ja307207q