Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles

• Guillaume G. Launay,
• Alexandra M. Z. Slawin and
• David O'Hagan

Beilstein J. Org. Chem. 2010, 6, No. 41, doi:10.3762/bjoc.6.41

• . Keywords: 4-fluoropiperidine; 4-fluoropyran; heterocycles; organo-fluorine chemistry; Prins cyclisation; Introduction Selective incorporation of the C–F bond into organic molecules can impart useful and attractive properties to performance materials [1][2][3]. To this end there are a useful but relatively

• donating groups on the aromatic ring (Table 1, entries h–j), the reactions were inefficient and conversions dropped dramatically. The saturated aliphatic aldehyde, hexanal (entry k), resulted in a good conversion, although the corresponding 4-fluoropyran products were obtained with poor