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J Org Chem. 2002 Oct 18;67(21):7429-31.

Mild alpha-halogenation reactions of 1,3-dicarbonyl compounds catalyzed by Lewis acids.

Author information

1
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. China. yangdan@hku.hk

Abstract

Lewis acid Mg(ClO4)2, combined with NBS, in CH3CN or EtOAc provided mild and fast bromination of 1,3-dicarbonyl compounds. In particular, this protocol could be applied to the alpha-monobromination of alpha-unsubstituted beta-keto esters. Similar Lewis acid catalysis was also extended to the alpha-chlorination and iodination of 1,3-dicarbonyl compounds with NCS and NIS, respectively.

PMID:
12375975
DOI:
10.1021/jo026025t

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