Reaction between N-(Thio)Phosphoryl Imines and Diethylzinc

The reaction between N-(thio)phosphoryl imines and diethylzinc was investigated in detail. For the imines bearing at least one P-O single bond, the corresponding reduction product was formed in excellent yield in nonpolar solvent toluene. In polar solvent, the reduction product was generated accompanied with partial formation of the alkylation product. The corresponding ethylating product became the predominant product in the presence of strong coordinative additive, such as N,N,N',N'-tetramethylethane-1,2-diamine (TMEDA).