Synlett 2004(7): 1219-1222  
DOI: 10.1055/s-2004-825599
LETTER
© Georg Thieme Verlag Stuttgart · New York

C-C Bond Formation between Isocyanide and β,β-Difluoroalkene Moieties via Electron Transfer: Fluorinated Quinoline and Biquinoline Syntheses

Junji Ichikawa*a, Takashi Moria, Hiroyuki Miyazakib, Yukinori Wadaa
a Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
Fax: +81(3)58414345; e-Mail: junji@chem.s.u-tokyo.ac.jp;
b Department of Applied Chemistry, Kyushu Institute of Technology, Sensui-cho, Tobata, Kitakyushu 804-8550, Japan
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Publication History

Received 5 March 2004
Publication Date:
10 May 2004 (online)

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Abstract

o-Isocyano-substituted β,β-difluorostyrenes are reduced with tributylstannyllithium to the anionic species, which in turn undergo intramolecular substitution of the isocyano carbon for the vinylic fluorine, followed by reaction with electrophiles or self-coupling to afford 2,4-disubstituted 3-fluoroquinolines or 4,4′-di­substituted 3,3′-difluoro-2,2′-biquinolines, respectively, in good yield.