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Hydrogen fluoride pyridine complex is used to prepare beta-fluoroamines via reaction with amino alcohols. As a fluorinating agent, is involved in the fluorination of 2,2-diary-1,3-dithiolanes. It is associated with nitrosonium tetrafluorborate to prepare gem-difluorides by reacting with ketoximes. It is also used to convert secondary and tertiary alcohols into their respective alkyl fluorides.
Convenient form of anhydrous HF, showing increased reactivity in many reactions: J. Org. Chem., 44, 3872 (1979). Alkenes and alkynes undergo hydrofluorination; in the presence of NIS or NBS, iodo- or bromofluorination occurs: Synthesis, 779 (1973). Secondary and tertiary alcohols are converted to alkyl fluorides: Synthesis, 653 (1974). Diazotization of ɑ-amino acids in the presence of the reagent provides good yields of ɑ-fluoro acids: Synthesis, 654 (1974). Reaction with aryldiazonium salts or triazenes leads to aryl fluorides, providing a convenient alternative to the Balz-Schiemann reaction (see Tetrafluoroboric acid, L14037): J. Am. Chem. Soc., 97, 208 (1975); J. Chem. Soc., Chem. Commun., 914 (1979); Bull. Chem. Soc. Jpn., 63, 2058 (1990).
In combination with nitrosonium tetrafluorborate, ketoximes are converted to gem-difluorides: Synlett, 425 (1994).
For use in electrophilic electrochemical fluorination, see: J. Fluorine Chem., 83, 31 (1997).
The reagent is also widely applied to the cleavage of a variety of silyl protecting groups including TBDMS, TES, TBDPS and TIPS: Synthesis, 453 (1986); J. Am .Chem. Soc., 112, 7001 (1990); for further discussion see: P. Kocienski, Protecting Groups, Thieme, Stuttgart (1994).
Metayer, B.; Compain, G.; Jouvin, K.; Martin-Mingot, A.; Bachmann, C.; Marrot, J.; Thibaudeau, S. Chemo-and Stereoselective Synthesis of Fluorinated Enamides from Ynamides in HF/Pyridine: Second-Generation Approach to Potent Ureas Bioisosteres. J. Org. Chem. 2015, 80 (7), 3397-3410.
Wang, Q.; Zhong, W.; Wei, X.; Ning, M.; Meng, X.; Li, Z. Metal-free intramolecular aminofluorination of alkenes mediated by PhI (OPiv) 2/hydrogen fluoride-pyridine system. Org. Biomol. Chem. 2012, 10 (43), 8566-8569.
Hazard Statements: H300-H310-H330-H314-H318
Fatal if swallowed. Fatal in contact with skin. Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P301+P310a-P303+P361+P353-P304+P340-P305+P351+P338-P320-P405-P501a
IF SWALLOWED: Immediately call a POISON CENTER/doctor IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment is urgent (see label). Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.