Reactions of ortho-substituted α,α-dibromoacetophenones with nucleophiles: first examples of combined carbophilic and bromophilic attack on C-Br bonds
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An efficient method for the formation of α-carbonyl-monosubstituted acetophenones from ortho-methoxy- and ortho-hydroxy-α,α-dibromoacetophenones and a range of selected nucleophiles, occurring via a carbophilic substitution/bromophilic substitution/protonation cascade process, is described. In turn, the preparation of α,α-dibromoacetophenones, isolated in high yields, relies on the neighboring group participation of the ortho-substituents in the starting ortho-substituted acetophenones.
Source:Tetrahedron Letters, 2009, 50, 6, 700-703
- Pergamon-Elsevier Science Ltd, Oxford