I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrC1C=CC=CC=1.C(P)=CC=C.[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])#[N:21].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C>[C:20]([CH2:22][C:23]([O:25][CH2:26][CH2:27][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:24])#[N:21]
The general procedure (acetonitrile, 82° C., 12 hours with iodobenzene; 30 hours in the case of bromobenzene) was followed using 9.52 mg (0.05 mmol) of copper iodide CuI, 31.4 mg (0.1 mmol) of (Z)-cinnamic butadienylphosphine of example A-1-1, 80 ml (0.75 mmol) of ethyl cyanoacetate, 318 mg (1.5 mmol) of potassium phosphate (K3PO4), 56 μl (0.5 mmol) of iodobenzene (53 μl of bromobenzene) and 500 μl of acetonitrile. The residue obtained after treatment (dichloromethane/water extraction) was purified by chromatography on a silica column (gradient: hexanes/CH2Cl2 100:0 to 75:25).
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