Fluoromethane aromatic substitution

In a series of comparative studies Dolle et al. examined the nucleophilic aromatic substitution of a number of nitropyridine derivatives [104—106], The results, as summarized in Scheme 13.14, show that under microwave-enhanced conditions the 2-N02 and 2-+NMe3 groups led to excellent fluorine incorporation whilst the 2-iodo compound was virtually unreactive. Under thermal conditions no fluorination was observed for the 2-chloro and 2-bromo compounds. In a separate study Banks et al. [107] again observed the beneficial effects of nitro and trimethylamino substitution (Scheme 13.15). The authors also developed a novel microwave-enhanced method of producing [18F]-fluoromethane [108]. 

---