Synthesis of (Hetero)Aroyl Fluorides via a Mild Amides C−N Bond Cleavage
Muhammad Aliyu Idris, Kwang Ho Song, Sunwoo Lee
Abstract
Abstract Amides, such as N ‐benzoylsaccharin, N,N ‐diBocbenzamide, and N ‐phenyl‐ N ‐tosylbenzamides reacted with Et 3 N⋅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. magnified image
Topics & Concepts
ChemistryCatalysisHalideAlkoxy groupSolventMedicinal chemistryBond cleavageCleavage (geology)Transition metalEnvironmentally friendlyOrganic chemistryFunctional groupReaction conditionsAlkylGeotechnical engineeringEngineeringBiologyFracture (geology)EcologyPolymerFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions