Indoline Catalyzed Acylhydrazone/Oxime Condensation under Neutral Aqueous Conditions

Journal Article (2020)
Author(s)

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)

Research Group
ChemE/Advanced Soft Matter
Copyright
© 2020 Yuntao Zhou, I. Piergentili, Jennifer Hong, M. van der Helm, M. Macchione, Y. Li, R. Eelkema, Sanzhong Luo
DOI related publication
https://doi.org/10.1021/acs.orglett.0c02128
More Info
expand_more
Publication Year
2020
Language
English
Copyright
© 2020 Yuntao Zhou, I. Piergentili, Jennifer Hong, M. van der Helm, M. Macchione, Y. Li, R. Eelkema, Sanzhong Luo
Research Group
ChemE/Advanced Soft Matter
Issue number
15
Volume number
22
Pages (from-to)
6035-6040
Reuse Rights

Other than for strictly personal use, it is not permitted to download, forward or distribute the text or part of it, without the consent of the author(s) and/or copyright holder(s), unless the work is under an open content license such as Creative Commons.

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.

Files

OL_Indoline_final_postprint.do... (docx)
(docx | 0.962 Mb)
- Embargo expired in 29-07-2021
License info not available