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

Dan Yang; Yi-Long Yan; Bob Lui

doi:10.1021/jo026025t

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

J Org Chem. 2002 Oct 18;67(21):7429-31. doi: 10.1021/jo026025t.

Authors

Dan Yang¹, Yi-Long Yan, Bob Lui

Affiliation

¹ Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. China. [email protected]

PMID: 12375975
DOI: 10.1021/jo026025t

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.