Grignard-type Reaction through the Generation of Oraganometal Reagent from Carboxylates

乙酸烯丙酯和乙醛的混合物在1，10-二氮杂菲镍催化剂、锌粉和碘化钠的存在下，在非质子溶剂中加热。得到的混合物以良好的产率得到了所需的高烯丙醇。在这种转化中，酯底物的烯丙基经历了Upolung，得到了亲核物种。生成的物种攻击醛底物的羰基碳。碘离子可以促进电子从锌粉向镍原子的转移。

A mixture of allyl acetate and an aldehyde was heated in an aprotic solvent in the presence of 1,10-phenanthroline-nickel catalyst, zinc powder, and sodium iodide. The resulting mixture gave the desired homoallyl alcohol in good yield. In this transformation, the allyl group of the ester substrate undergoes umpolung to give a nucleophilic species. The resulting species attacks the carbonyl carbon of the aldehyde substrate. The iodide anion may facilitate the electron transfer from zinc powder to the nickel atom.