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31.1.1.5.1.1 Variation 1: Reaction with Potassium Fluoride

DOI: 10.1055/sos-SD-031-00002

Sandford, G.Science of Synthesis, (20073153.

Nitro groups are more labile than chlorine atoms in many nucleophilic aromatic substitution processes. This behavior has been exploited in many fluorodenitration processes in which nitro groups are displaced by fluorine through reaction of a suitably activated nitroaromatic substrate with a source of fluoride ion (Table 13).[‌124‌,‌126‌,‌127‌] An example is the conversion of 2-nitrothiazole (45) into 2-fluorothiazole (46). As with halogen-exchange processes, the nitroaromatic substrate must possess electron-withdrawing substituents to be sufficiently active toward nucleophilic attack and give acceptable yields. Fluorodenitration permits the synthesis of products in which fluorine is located meta to other electron-withdrawing groups, unlike related halogen-exchange processes where the corresponding transformation is very difficult. Consequently, fluorodenitration offers a fluoride-ion based methodology that is complementary to halogen-exchange reactions.[‌125‌]

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