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

Chemical Science
Dennis LarsenEric T Kool

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.

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Mar 7, 2019·Organic & Biomolecular Chemistry·Patrick L HiggsDavid A Fulton
Apr 13, 2019·Macromolecular Rapid Communications·Zhen JiangLuke A Connal
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Oct 27, 2020·Organic Letters·Nathalie OllivierOleg Melnyk
Jan 25, 2019·Accounts of Chemical Research·Sébastien Ulrich
Jul 7, 2021·Communications Biology·Huilei WangLakshmi Santhanam

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