Multi-step reaction with 10 steps
1.1: triphenylphosphine / CH2Cl2 / 0.5 h / -20 °C
1.2: 86 percent / triethylamine / CH2Cl2 / 0.5 h / 0 °C
2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 2 h / -78 °C
2.2: 82 percent / tetrahydrofuran; hexane / 2.5 h / 20 °C
3.1: 96 percent / carbon tetrachloride; triphenylphosphine; sodium bicarbonate / 4 h / Heating
4.1: 85 percent / lithium amide / tetrahydrofuran; hexamethylphosphoric acid triamide; liquid ammonia / 0.5 h
5.1: 88 percent / imidazole / CH2Cl2 / 24 h / 20 °C
6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
6.2: BF3*OEt2 / tetrahydrofuran; hexane / 0.5 h / -78 °C
6.3: 75 percent / tetrahydrofuran; hexane / 1 h / -78 °C
7.1: 91 percent / imidazole / CH2Cl2 / 6 h / 20 °C
8.1: 94 percent / CuCl2*2H2O / acetonitrile / 3 h / 20 °C
9.1: 89 percent / triphenylphosphine; I2; imidazole / toluene / 3 h / Heating
10.1: 82 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 1 h / 20 °C
With
1H-imidazole; tetrachloromethane; n-butyllithium; lithium amide; iodine; sodium hydrogencarbonate; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; ammonia; water; toluene; acetonitrile;
DOI:10.1016/S0040-4020(02)00423-4