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

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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.