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Synthesis 2010(12): 2080-2084  
DOI: 10.1055/s-0029-1218754
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Sodium Bromodifluoroacetate: A Difluorocarbene Source for the Synthesis of gem-Difluorocyclopropanes

Kojun Oshiro, Yoshimichi Morimoto, Hideki Amii*
Department of Chemistry, Graduate School of Science, Kobe University, Nada-ku 1-1, Kobe 657-8510, Japan
Fax: +81(78)8035799; e-Mail: amii@kobe-u.ac.jp;
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Publication History

Received 24 February 2010
Publication Date:
23 April 2010 (online)

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Abstract

As a new difluorocarbene source, sodium bromodifluoroacetate (BrCF2CO2Na) was found to be effective for high-yielding­ synthesis of gem-difluorocyclopropanes and gem-difluorocyclopropenes under mild conditions.

Key words

fluorine - carbenes - cycloaddition - cyclopropanes - cyclopropenes­

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21

The formation of 5 and 6 can be explained by assuming the following pathway (Scheme  [4] ).

Scheme 4

23

Bromodifluoroacetic acid is available from SynQuest Laboratories, Inc. (www. synquestlabs.com).