Para-Fluorination of Anilides Using Electrochemically Generated Hypervalent Iodoarenes

Area of Science:

• Organic Chemistry
• Electrochemistry
• Fluorination Reactions

Background:

• Selective fluorination of aromatic compounds is crucial in medicinal chemistry and materials science.
• Traditional methods often require harsh reagents or complex procedures.
• Electrochemical approaches offer a sustainable and controlled alternative for synthetic transformations.

Purpose of the Study:

• To develop a novel, efficient, and scalable electrochemical method for para-selective fluorination of anilides.
• To utilize electrochemically generated hypervalent iodine reagents for direct fluorination.
• To explore the scope and limitations of this new synthetic methodology.

Main Methods:

• Para-selective fluorination of anilides was achieved using electrochemically generated hypervalent ArIF2.
• Triethylamine trihydrofluoride (Et3N·5HF) served as both the fluoride source and supporting electrolyte.
• The electrochemical reaction was performed using a simple, scalable set-up.

Main Results:

• The method successfully fluorinated a broad range of easily accessible anilides.
• Good to excellent yields, up to 86%, of the desired para-fluorinated anilides were obtained.
• The reaction demonstrated high para-selectivity, minimizing the formation of undesired isomers.

Conclusions:

• This work presents a practical and efficient electrochemical strategy for the synthesis of para-fluorinated anilides.
• The methodology is characterized by its simplicity, scalability, and broad substrate scope.
• This approach provides a valuable tool for accessing fluorinated organic molecules.