Indoline Catalyzed Acylhydrazone/Oxime Condensation under Neutral Aqueous Conditions
Yuntao Zhou, Irene Piergentili, Jennifer Hong, Michelle P. van der Helm, Mariano Macchione, Yao Li, Rienk Eelkema, Sanzhong Luo
Abstract
Acylhydrazones formation has been widely applied in materials science and biolabeling. However, their sluggish condensation rate under neutral conditions limits its application. Herein, indolines with electron-donating groups are reported as a new catalyst scaffold, which can catalyze acylhydrazone, hydrazone, and oxime formation via an iminium ion intermediate. This new type of catalyst showed up to 15-fold rate enhancement over the traditional aniline-catalyzed reaction at neutral conditions. The identified indoline catalyst was successfully applied in hydrogel formation.
Topics & Concepts
ChemistryIndolineOximeCatalysisIminiumAnilineHydrazoneAqueous solutionCondensationCombinatorial chemistryOrganic chemistryPhysicsThermodynamicsChemical Synthesis and AnalysisClick Chemistry and ApplicationsSynthesis and Catalytic Reactions