Aniline Catalysed Hydrazone Formation Reactions Show a Large Variation in Reaction Rates and Catalytic Effects

Fanny Trausel, Bowen Fan, Susan A.P. van Rossum, Jan H. van Esch, Rienk Eelkema

Research output: Contribution to journalArticleScientificpeer-review

8 Citations (Scopus)
23 Downloads (Pure)

Abstract

Hydrazone formation reactions from aldehydes and hydrazides have the remarkable qualities that they proceed in water and the kinetics can be controlled by organocatalysis. For these reasons, this class of reactions finds widespread use in biological as well as material settings. We recently reported a protected aniline catalyst for hydrazone formation that can be activated using a chemical signal. In our search to find a suitable hydrazone formation reaction to investigate the activation of this pro-catalyst, we found a wide variety in reaction rates and response to catalysis. Here we report an overview of hydrazone formation reactions, their reaction rates and response to aniline catalysis, their compatibility for kinetic analysis by UV/Vis spectroscopy, and their compatibility with the reaction environment and with the pro-catalyst pro-aniline.

Original languageEnglish
Article number201800342
Pages (from-to)1-7
JournalAdvanced Synthesis and Catalysis
Volume360
DOIs
Publication statusPublished - 2018

Keywords

  • Bioorthogonal chemistry
  • Click chemistry
  • Hydrazones
  • Organocatalysis
  • UV/vis spectroscopy

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