| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1315493 | Journal of Fluorine Chemistry | 2008 | 8 Pages |
The regiochemistry of nucleophilic substitution of 4-bromo-2,3,5,6-tetrafluoropyridine has been investigated. Efficient, regioselective reactions occur with alkylamine, benzylamine and alkoxide nucleophiles, yielding products where substitution occurs ortho to the ring nitrogen. The resulting 2-substituted-4-bromo-3,5,6-trifluoropyridines can be functionalised further, either by a second regioselective nucleophilic displacement or palladium catalysed elaboration at the 4-position. Reactions with aromatic N-nucleophiles yield mixtures of ortho- and para-substituted products.
Graphical abstractThe regiochemistry of sequential nucleophilic substitution and palladium catalysed Suzuki–Miyaura reactions of 4-bromo-2,3,5,6-tetrafluoropyridine has been investigated. Figure optionsDownload full-size imageDownload as PowerPoint slide
