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31.1.1.5.2.5 Variation 5: Reaction with Nitrosonium Tetrafluoroborate

DOI: 10.1055/sos-SD-031-00002

Sandford, G.Science of Synthesis, (20073164.

A useful variation on the BalzSchiemann reaction (see Section 31.1.1.5.2.3) involves the use of commercially available nitrosonium tetrafluoroborate, which acts as both the diazotizing and the fluorinating agent.[‌154‌] The nonacidic conditions of this process facilitate the fluorination of aromatic amines 60 bearing acid-sensitive functional groups, such as ester, aldehyde, or N-acetyl substituents (Scheme 33). However, the relatively high cost of the nitrosonium tetrafluoroborate probably limits the use of this method to small-scale syntheses of fluoroarenes 61.

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