Removal of fluorine from and introduction of fluorine into polyhalopyridines: An exercise in nucleophilic hetarenic substitution
Starting from six industrially available fluorinated pyridines, an expedient access to all three tetrafluoropyridines (2-4), all six trifluoropyridines (5-10), and the five non-commercial difluoropyridines (11-14 and 16) was developed. The methods employed for the selective removal of fluorine from polyfluoropyridines were the reduction by metals or complex hydrides and the site-selective replacement by hydrazine followed by dehydrogenation-dediazotation or dehydrochlorination-dediazotation. To introduce an extra fluorine atom, a suitable precursor was metalated and chlorinated before being subjected to a chlorine/ fluorine displacement process.
Bobbio, Carla,Rausis, Thierry,Schlosser, Manfred
p. 1903 - 1910
(2007/10/03)
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