Download PDF
Synthesis 2002(4): 0533-0537
DOI: 10.1055/s-2002-20969
PAPER
© Georg Thieme Verlag Stuttgart · New York

Cyclopropane Formation by Copper-Catalysed Indirect Electroreductive Coupling of Activated Olefins and Activated α,α,α-Trichloro or Gem-Dichloro Compounds

S. Sengmany, E. Léonel, J. P. Paugam*, J.-Y. Nédélec
LECSO-CNRS UMR 7582, Université Paris XII, Val de Marne, 2 à 8 rue H. Dunant 94320 Thiais, France
Fax: +33(1)49781148; e-Mail: paugam@glvt-cnrs.fr;
Further Information

Publication History

Received 20 November 2001
Publication Date:
28 July 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

Cyclopropanes have been prepared in good yields by indirect electroreductive coupling of activated olefins and activated α,α,α-trichloro or gem-dichloro compounds (Cl3CCO2Me, PhCCl3, Ph2CCl2, PhCHCl2). This process, using a copper complex in catalytic amountss is convenient for the reagent couple activated olefin/activated polyhalide, whatever the reduction potential of each reagent relative to each other. The main advantage of our electrochemical process is that it does not require the use of hazardous, toxic, or not easily prepared reagents like diazocompounds or diazirines.

Key words

cyclopropanation - electro-organic synthesis - carbenoids