Multi-step reaction with 7 steps
1.1: 91 percent / NaI / acetone / 20 h / 20 °C
2.1: CuI / tetrahydrofuran / 0.5 h / 20 °C
2.2: 75 percent / tetrahydrofuran / 0.5 h / -48 °C
3.1: 93 percent / NaCN / methanol / 20 h / 50 °C
4.1: KHMDS / toluene; tetrahydrofuran / 1 h / -78 °C
4.2: 82 percent / toluene; tetrahydrofuran / 20 h / -78 °C
5.1: 82 percent / cerium(III) chloride / tetrahydrofuran / 1 h / -48 °C
6.1: 87 percent / Ph-CH=Ru(PCy3)Cl2(1,3-MeS2-imidazolidin-2-yl) / CH2Cl2 / 2 h / Heating
7.1: tert-butyllithium / diethyl ether; pentane; toluene / -78 - 0 °C
7.2: 56 percent / Me3Al / toluene / 2 h / -78 °C
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; copper(l) iodide; cerium(III) chloride; sodium cyanide; tert.-butyl lithium; potassium hexamethylsilazane; sodium iodide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene; pentane;
DOI:10.1021/ja044753n