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[reaction: see text] Under the Lewis acid catalysis offered by TiCl(3), SnCl(2) can efficiently mediate the aqueous Barbier reactions between aldehydes and allyl chloride or bromide.

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Copper was found to be able to promote the SnClz-mediated carbonyl allylation reactions in water, giving the corresponding homoallylic alcohol products in very high yields. Detailed studies showed that the reaction could be applied to a variety of carbony1 compounds including those with hydroxyl, amino and nitro groups. It was also found that this reaction showed good regioselectivities for some substrates. Furthermore, carefully controled experiments and in situ NMR measurements provided important insights into the mechanism of the newly developed reaction.