Multi-step reaction with 11 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C
1.2: 2 h / -78 °C
2.1: Hoveyda-Grubbs catalyst second generation / toluene / Reflux
3.1: N,N,N'N'-tetramethyl-1,3-propanediamine / toluene / 1 h / 0 - 20 °C
4.1: sodium tetrahydroborate / ethanol / 14 h / 0 - 20 °C
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 6.5 h / 0 - 20 °C / pH 6.6
6.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C
7.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 7 h / 0 - 20 °C
8.1: triethylamine; lithium hexamethyldisilazane / tetrahydrofuran / 3.5 h / -78 °C
9.1: palladium diacetate / dimethyl sulfoxide / 18 h / 20 °C
10.1: lithium hexamethyldisilazane / tetrahydrofuran / 22 h / -40 °C
11.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; hexane / 24 h / 0 - 20 °C
With
dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); Hoveyda-Grubbs catalyst second generation; N,N,N'N'-tetramethyl-1,3-propanediamine; palladium diacetate; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; tert-butyl alcohol;
11.1: Negishi coupling reaction;
DOI:10.1002/anie.201201383