Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)
William D. G. Brittain, Steven L. Cobb
Abstract
This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.
Topics & Concepts
ChemistryReagentAmideCarboxylic acidPeptide bondOrganic chemistryCombinatorial chemistryEnzymeChemical Synthesis and AnalysisFluorine in Organic ChemistryCarbohydrate Chemistry and Synthesis