Synthesis of (Hetero)Aroyl Fluorides via a Mild Amides C-N Bond Cleavage

Amides, such as N-benzoylsaccharin, N,N-diBocbenzamide, and N-phenyl-N-tosylbenzamides reacted with Et3N.3HF to provide the corresponding acyl fluorides in good yields. The reaction was conducted under environmentally friendly conditions using i-PrOAc as the solvent. Moreover, the reaction was performed at room temperature and did not require a transition-metal catalyst or additives. The methodology showed functional group tolerance toward amines, alkoxy, halides, ketones, esters, and aldehydes.

Automated summary

This study presents a new method for synthesizing acyl fluorides under environmentally friendly conditions without the need for transition-metal catalysts or additives. The methodology demonstrates good functional group tolerance towards various groups.