Electrophilic Fluorination Agents

Electrophilic Fluorination Agents

Introduction

Electrophilic fluorination agents are a kind of fluorine source in the F⁺ form of fluorination. Electrophilic fluorination of electron-rich unsaturated compounds such as arenes and alkenes using electrophilic fluorination agents is a reliable strategy to obtain fluorinated compounds. Fluorine-containing compounds have important applications in organic chemistry, medicinal chemistry, agricultural chemistry and materials science. Their preparation and development has become a research hotspot in organic synthesis methodology in recent years. At present, more and more electrophilic fluorination agents are used in the synthesis of fluorinated compounds, which have become an important field of fluorination research and application.

Common Electrophilic Fluorination Agents

Commonly used electrophilic fluorination agents are N-fluoropyridinium salts (NFPy), N-fluorobenzenesulfonimide (NFSI), 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF₄) and its derivative (1-fluoro-4-hydroxy-1,4-diazoniabicyclo-[2,2,2]octane bis(tetrafluoroborate)) (NFTh).

• NFPy. NFPy are of great interest from the point of view of their unique stability, reactivity, and highly interesting possibilities in synthesis. Their fluorinating ability is variable, and by changing the substituent on the pyridine ring, fluorination agents with different fluorination abilities can be designed according to needs. They are mainly used for the fluorination of various enol compounds, multi-electron aromatic compounds, sulfides, etc., especially for the fluorination of compounds that containing multiple complex functional groups.
• NFSI. NFSI is an economical, stable and safe fluorination agent, which has high fluorination ability and electrophilicity, and is soluble in various organic solvents. It can fluorinate compounds such as olefins, aromatic hydrocarbons, amides, and nitriles.
• F-TEDA-BF₄. F-TEDA-BF₄ is an electrophilic fluorination agent with stable properties, mild use conditions and wide applications. It has the characteristics of high thermal stability, low toxicity and strong oxidizing properties. And it can be used to fluorinate enamines, dicarbonyl compounds, and electron-rich aromatic compounds, and obtain fluorinated products in high yield.
• NFTh. NFTh is confirmed as a highly effective electrophilic fluorination agent, also known as a versatile electrophilic fluorination agent. It is safe and easy to handle, and is widely used to fluorinate aromatic rings, olefins, dienol acetates enol ethers, etc.

Fig.1 Commonly used electrophilic fluorination agents

Applications

Electrophilic fluorination agents are widely used in the synthesis of fluorinated compounds in organic chemistry. They are efficient and easy to operate, and can fluorinate aromatic rings, carbonyl compounds, olefins, thioethers, etc. under mild reaction conditions. Electrophilic fluorination agents can introduce fluorine into the aromatic ring by electrophilic reaction to fluorinate aromatic ring compounds, or introduce fluorine atoms at the alpha position of carbonyl to fluorinate carbonyl compounds, or react with olefins or arylalkyl substituted styrene to generate Markovnikov addition-type fluorinated products, or react with thioethers containing α-H to generate α-fluorosulfides.

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