4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 21, Pages 7429-7431

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo026025t

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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.

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