Bromophilic substitution/carbophilic substitution cascade reactions of alpha,alpha-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles
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alpha,alpha-Dibromo-2-methoxyacetophenone reacts, under mild reaction conditions, with C-, N- and O-nucleophiles via a bromophilic substitution/protonation/carbophilic substitution cascade process to afford alpha-monosubstituted-2-methoxyacetophenones in moderate to good yield. The only exception from this reaction pathway is the reaction with the anion derived from malononitrile in which 2-aroyl-1,1,3,3-tetracyanopropene is obtained.
Keywords:alpha,alpha-Dibromomethylketone / Bromophilic reaction / Nucleophilic substitution / Cascade reactions
Source:Tetrahedron Letters, 2010, 51, 37, 4851-4855
- Pergamon-Elsevier Science Ltd, Oxford