Beyond Amide Bond Formation: TCFH as a Reagent for Esterification
Nathaniel R. Luis, Kasey K. Chung, Matthew Hickey, Ziqing Lin, Gregory L. Beutner, David A. Vosburg
Abstract
In this Communication, an investigation of the combination of N, N, N ′, N ′-tetramethylchloroformamidinium hexafluorophosphate (TCFH) and N -methylimidazole (NMI) for the synthesis of esters and thioesters is described. This work revealed the unique challenges of the reactions of less nucleophilic alcohols and more reactive thiols with the N -acyl imidazolium intermediate and led to the identification of general enabling conditions that provide high yields and selectivity for a range of alcohols and thiols.
Topics & Concepts
ChemistryHexafluorophosphateReagentNucleophileAmideSelectivityCombinatorial chemistryPeptide bondOrganic chemistryIonic liquidCatalysisEnzymeChemical Synthesis and ReactionsChemical Synthesis and AnalysisSulfur-Based Synthesis Techniques