Indoline Catalyzed Acylhydrazone/Oxime Condensation under Neutral Aqueous Conditions
Yuntao Zhou (Tsinghua University)
Irene Piergentili (TU Delft - ChemE/Advanced Soft Matter)
Jennifer Hong (Student TU Delft)
M.P. van der Helm (TU Delft - ChemE/Advanced Soft Matter)
M. Macchione (TU Delft - ChemE/Advanced Soft Matter)
Y. Li (Tsinghua University)
R Eelkema (TU Delft - ChemE/Advanced Soft Matter)
Sanzhong Luo (Tsinghua University)
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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.