Indoline Catalyzed Acylhydrazone/Oxime Condensation under Neutral Aqueous Conditions

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,...

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Bibliographic Details
Published in:Organic letters 2020-08, Vol.22 (15), p.6035-6040
Main Authors: Zhou, Yuntao, Piergentili, Irene, Hong, Jennifer, van der Helm, Michelle P, Macchione, Mariano, Li, Yao, Eelkema, Rienk, Luo, Sanzhong
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02128