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

Research output: Contribution to journalArticleScientificpeer-review

2 Citations (Scopus)
2 Downloads (Pure)


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.

Original languageEnglish
Pages (from-to)6035-6040
Number of pages6
JournalOrganic Letters
Issue number15
Publication statusPublished - 2020

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