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Boron (III) Tribromide or Titanium (IV) Bromide and Lewis Base Promoted Baylis‐Hillman Reaction
Author(s) -
Shi Min,
Cui ShiCong
Publication year - 2002
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.20020200313
Subject(s) - chemistry , allylic rearrangement , bromide , catalysis , lewis acids and bases , adduct , methyl vinyl ketone , tribromide , organic chemistry , ketone , titanium , amine gas treating , medicinal chemistry , boron
Abstract It was found that, when the Baylis‐Hillman reaction of arylaldehydes with methyl vinyl ketone was carried out at below ‐20 °C in the presence of boron (III) tribromide or titanium (IV) bromide using a catalytic amount of Lewis base such as amine, the brominated compounds and the Baylis‐Hillman adducts could be obtained as the major products in good yields for various aryl aldehydes. But at room temperature, the elimination products were the major products. In addition, the palladium catalyzed allylic substitution reactions of the elimination products were also examined.