Synthesis 2013; 45(18): 2600-2604
DOI: 10.1055/s-0033-1338515
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium(II)-Catalyzed Sequential C−Cl Bond Formation: A Novel and Efficient Method for Direct α,α-Dichlorination of β-Dicarbonyl Compounds

Authors

  • Weibing Liu*

    School of Chemistry and Life Science, Guangdong University of Petrochemical Technology, 2 Guangdu Road, Maoming 525000, P. R. of China   Fax: +86(68)2923529   Email: lwb409@gmail.com
  • Liquan Tan

    School of Chemistry and Life Science, Guangdong University of Petrochemical Technology, 2 Guangdu Road, Maoming 525000, P. R. of China   Fax: +86(68)2923529   Email: lwb409@gmail.com
  • Peng Zhou

    School of Chemistry and Life Science, Guangdong University of Petrochemical Technology, 2 Guangdu Road, Maoming 525000, P. R. of China   Fax: +86(68)2923529   Email: lwb409@gmail.com
  • Cui Chen

    School of Chemistry and Life Science, Guangdong University of Petrochemical Technology, 2 Guangdu Road, Maoming 525000, P. R. of China   Fax: +86(68)2923529   Email: lwb409@gmail.com
  • Qing Zhang

    School of Chemistry and Life Science, Guangdong University of Petrochemical Technology, 2 Guangdu Road, Maoming 525000, P. R. of China   Fax: +86(68)2923529   Email: lwb409@gmail.com
Further Information

Publication History

Received: 08 May 2013

Accepted after revision: 11 July 2013

Publication Date:
09 August 2013 (online)


Graphical Abstract

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.

Supporting Information