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Synthesis 2013; 45(18): 2600-2604
DOI: 10.1055/s-0033-1338515
DOI: 10.1055/s-0033-1338515
paper
Palladium(II)-Catalyzed Sequential C−Cl Bond Formation: A Novel and Efficient Method for Direct α,α-Dichlorination of β-Dicarbonyl Compounds
Further Information
Publication History
Received: 08 May 2013
Accepted after revision: 11 July 2013
Publication Date:
09 August 2013 (online)


Abstract
A simple and concise procedure for the synthesis of 2,2-dichloro-3-oxo-N-phenylbutanamides, via palladium-catalyzed C(sp3)–H dichlorination of 3-oxo-N-phenylbutanamides, is described. The protocol provides a direct route to α,α-dichlorinated products starting from β-dicarbonyl compounds. A plausible mechanism for this transformation involving two consecutive chlorination steps is described.
Key words
2,2-dichloro-3-oxo-N-phenylbutanamides - β-dicarbonyl compounds - dichlorination - carbon–chlorine bondSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information