Multi-step reaction with 10 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C
1.2: 0.75 h / -78 - 0 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C
2.2: 6 h / -50 °C
3.1: lithium borohydride / tetrahydrofuran / 0 °C
4.1: 1H-imidazole / dichloromethane / 20 °C
5.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -40 °C
6.1: triphenylphosphine; carbon tetrabromide / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
7.1: N,N,N,N,-tetramethylethylenediamine; iron(III) chloride / tetrahydrofuran / 0.5 h / 0 °C
8.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / N,N-dimethyl-formamide / 7 h / 140 °C / Inert atmosphere
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C
With
1H-imidazole; iron(III) chloride; lithium borohydride; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; carbon tetrabromide; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; triphenylphosphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
8.1: |Heck Reaction;
DOI:10.1016/j.tet.2013.10.064