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Issue 23, 2018
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Exceptionally rapid oxime and hydrazone formation promoted by catalytic amine buffers with low toxicity

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Abstract

Hydrazone and oxime bond formation between α-nucleophiles (e.g. hydrazines, alkoxy-amines) and carbonyl compounds (aldehydes and ketones) is convenient and is widely applied in multiple fields of research. While the reactants are simple, a substantial drawback is the relatively slow reaction at neutral pH. Here we describe a novel molecular strategy for accelerating these reactions, using bifunctional buffer compounds that not only control pH but also catalyze the reaction. The buffers can be employed at pH 5–9 (5–50 mM) and accelerate reactions by several orders of magnitude, yielding second-order rate constants of >10 M−1 s−1. Effective bifunctional amines include 2-(aminomethyl)imidazoles and N,N-dimethylethylenediamine. Unlike previous diaminobenzene catalysts, the new buffer amines are found to have low toxicity to human cells, and can be used to promote reactions in cellular applications.

Graphical abstract: Exceptionally rapid oxime and hydrazone formation promoted by catalytic amine buffers with low toxicity

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Supplementary files

Article information


Submitted
06 Mar 2018
Accepted
18 May 2018
First published
21 May 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 5252-5259
Article type
Edge Article

Exceptionally rapid oxime and hydrazone formation promoted by catalytic amine buffers with low toxicity

D. Larsen, A. M. Kietrys, S. A. Clark, H. S. Park, A. Ekebergh and E. T. Kool, Chem. Sci., 2018, 9, 5252
DOI: 10.1039/C8SC01082J

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