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Synfacts 2010(3): 0276-0276
DOI: 10.1055/s-0029-1219419
DOI: 10.1055/s-0029-1219419
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Pd-Catalyzed Synthesis of Fluoropiperidines
T. Wu, G. Yin, G. Liu*
Shanghai Institute of Organic Chemistry, P. R. of China
Further Information
Publication History
Publication Date:
18 February 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201003/lookinside/thumbnails/10.1055-s-0029-1219419-1.jpg)
Significance
Reported is the palladium-catalyzed intramolecular aminofluorination of unactivated alkenes 1 to give 3-fluoropiperidines 2. Substrates with either one (R² = H) or two (R² ∂ H) substituents at the β-position were well tolerated. Two examples containing disubstituted alkenes (R¹ = Me) were also shown to proceed in high yield. Opposite diastereoselectivities were observed in the reaction of trans-3 and cis-3 under the standard conditions. Substrate 6, containing one extra methylene unit in the linker, demonstrated a preference for 7-endo cyclization over 6-exo, in moderate combined yield.