Download PDF
Synthesis 2004(5): 701-705  
DOI: 10.1055/s-2004-815960
PAPER
© Georg Thieme Verlag Stuttgart · New York

The Development of a Novel Synthetic Method for Cyanofluoroamides Using a Cobaltadithiolene Complex

Yasuo Yokoyamaa, Shoko Suzukib, Hyuma Furihataa, Shunsuke Takahia, Mitsushiro Nomuraa, Masatsugu Kajitani*a
a Department of Chemistry, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan
Fax: +81(3)32383361; e-Mail: yasuo-y@sophia.ac.jp;
b Institute for Fundamental Research of Organic Chemistry, Kyushu University, Hakozaki, Fukuoka 812-8581, Japan
Further Information

Publication History

Received 5 December 2003
Publication Date:
09 February 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

N,N-Diethyl 2-cyano-2-fluoro-2-(phenylthio)aceto­amide (1) reacts with germyl anion species to give the corresponding enolates effectively. When this active species was treated with an unsaturated organic halide in the presence of a catalytic amount of a cobaltadithiolene complex, the desired compound was obtained in good yield. Interestingly, when the cobaltadithiolene complex was not used, no target product was obtained. This synthetic reaction proceeded smoothly under mild reaction conditions and only cyanofluoroamide was obtained.

Key words

germyl anion - cyanofluoroamide - cobaltadithiolene complex - allyl chloride - catalytic