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Fluorination [Synthetic Reagents]
Fig. 1 Fluorinated bioactive compounds
The most basic nucleophilic fluorinating agent is hydrogen fluoride which is used in large quantity for the industrial production of fluorinated compounds. Hydrogen fluoride (HF), however, is scarcely used in laboratories due to its toxic and corrosive properties and its low reactivity resulting from high H-F bond energy. Nucleophilic fluorinating agents such as KF, CsF, and Bu4N•F are readily available.
4-tert-Butyl-2,6-dimethylphenylsulfur trifluoride (FLUOLEAD™) [B3664], which was first reported by Umemoto, is a novel nucleophilic fluorinating reagent.2) FLUOLEAD is a white crystalline solid with high thermal stability, which has a 232 °C thermal decomposition temperature (by DSC analysis). Differing from other existing fluorinating reagents, such as DAST, FLUOLEAD has less fuming character. And the reactivity of FLUOLEAD to water is slow, which makes it easier to handle in open air. Fluorinations of a hydroxyl or carbonyl group by FLUOLEAD afford the corresponding fluorinated compounds in good yields under a wide range of conditions (0 to 100 °C).
The basic agent among electrophilic fluorinating agents is fluorine gas, which is not suitable for partial fluorination due to its vigorous reactivity and strong toxicity.
N-Fluoro-N'-(chloromethyl)triethylenediamine bis(tetrafluoroborate) [F0358] is an easily handled powder and versatile electrophilic fluorinating agent for enols, silyl enol ethers, alkenes, stabilized carbanions, aromatic compounds, organosulfur compounds, Grignard reagents, etc.3)
- Synthesis of Aryl Fluorides Using Electrophilic N-F Reagents
- PhenoFluor™ Mix and AlkylFluor™: Stable Reagents for Deoxyfluorinations
- Hypervalent Iodine-Catalyzed Balz–Schiemann Fluorination
- An Air- and Moisture- stable Electrophilic Fluorinating Reagent
- BF3•Et2O Functioning as a Fluorine Source in an PhIO mediated Intermolecular Aminofluorination
- Metal-Free Fluorination of C(sp3)-H Bonds using a Catalytic N-Oxyl Radical
- Stable Fluorinating Reagent with Ease of Handling (FLUOLEAD™)
- 1) a) T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470.
- 2) T. Umemoto, R. P. Singh, Y. Xu, N. Saito, J. Am. Chem. Soc. 2010, 132, 18199.
- 3) a) C. Zhou, J. Li, B. Lu, C. Fu, S. Ma, Org. Lett. 2008, 10, 581.