Nucleophilic Aromatic Substitution of 5-Bromo-1,2,3-triazines with Phenols
Han Luo, Yumeng Li, Yuan Zhang, Qixing Lu, Qiaoyu An, Mingchuan Xu, Shanshan Li, Jun Li, Baosheng Li
Abstract
Nucleophilic aromatic substitution (SNAr) reaction in classic textbook is a stepwise mechanism, and few examples of concerted reactions have been reported. Herein, we developed a concerted SNAr reaction of 5-bromo-1,2,3-triazines with phenols in which the nonclassic mechanism of this reaction could be revealed by calculation. Furthermore, the resulting 5-aryloxy-1,2,3-triazines could be used as convenient precursors to access biologically important 3-aryloxy-pyridines in one-pot manner.
Topics & Concepts
Nucleophilic aromatic substitutionChemistryPhenolsNucleophilic substitutionNucleophileSubstitution reactionOrganic chemistryRadical-nucleophilic aromatic substitutionReaction mechanismMedicinal chemistryCombinatorial chemistryCatalysisSynthesis and Characterization of Heterocyclic CompoundsChemical Reaction MechanismsClick Chemistry and Applications