Anhui Key Laboratory of Advanced Building Materials, Anhui University of Architecture, Hefei, Anhui 230022, China

A novel mediator (Al/KF) has been developed and employed in the Barbier-type alkylations of various aldehydes and ketones with alkyl halide in water. The carbonyl compounds could be effectively converted into corresponding homoallylic alcohol in good yields only when allyl bromides or substituted allyl bromides were used as halides. Aromatic aldehydes could afford homoallylic alcohols in high yields, unfortunately, the allylation of aromaticaldehyde substituted by nitro- or amino-group could not proceed smoothly, and the allylation yields of ketones and aliphatic carbonyl compounds were lower under the same condition. The diastereoselectivity and regioseletivity of the reaction have also been studied, the predominant products preferred the erythro- or anti-isomer in dominant γ-adduct by using Al/KF mediated allylation of benzaldehydes with cinnamyl bromide and ethyl 4-bromo-2-butenoate in water.