Synthesis of (Hetero)Aroyl Fluorides via a Mild Amides C−N Bond Cleavage,Advanced Synthesis & Catalysis

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Synthesis of (Hetero)Aroyl Fluorides via a Mild Amides C−N Bond Cleavage
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-06-03 , DOI: 10.1002/adsc.202200275
Muhammad Aliyu Idris ₁ , Kwang Ho Song ₂ , Sunwoo Lee ₃

Affiliation

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.

中文翻译：

通过温和的酰胺 C-N 键断裂合成 (杂) 芳酰氟

酰胺，例如N-苯甲酰糖精、 N,N-二苯甲酰胺和N-苯基-N-甲苯磺酰苯甲酰胺与 Et ₃ N·3HF 反应以良好的收率提供相应的酰氟。该反应在环境友好的条件下使用i- PrOAc 作为溶剂进行。此外，该反应在室温下进行，不需要过渡金属催化剂或添加剂。该方法显示官能团对胺、烷氧基、卤化物、酮、酯和醛的耐受性。

更新日期：2022-06-03

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