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Allylation of Carbonyl Compounds Mediated by Aluminum/Fluoride Salts in Water
Author(s) -
Yuan Shizhen,
Liu Jin,
Xu Ling,
Zhu Shaofeng
Publication year - 2010
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201090115
Subject(s) - chemistry , allyl bromide , aldehyde , adduct , halide , alcohol , organic chemistry , alkyl , bromide , carbonyl group , cinnamyl alcohol , medicinal chemistry , catalysis , cinnamaldehyde
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 aromatic aldehyde 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.