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

Title

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

 Author

Trausel, F. (TU Delft ChemE/Advanced Soft Matter)
Fan, B. (TU Delft ChemE/Advanced Soft Matter)
van Rossum, S.A.P. (TU Delft ChemE/Advanced Soft Matter)
van Esch, J.H. (TU Delft ChemE/Advanced Soft Matter) ORCID 0000-0001-6116-4808
Eelkema, R. (TU Delft ChemE/Advanced Soft Matter) ORCID 0000-0002-2626-6371

 Date

2018

 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.


 Subject

Bioorthogonal chemistry
Click chemistry
Hydrazones
Organocatalysis
UV/vis spectroscopy

 To reference this document use:

http://resolver.tudelft.nl/uuid:353ad115-08f5-4afc-8322-ef4e24eab25c

 DOI

https://doi.org/10.1002/adsc.201800342

 Embargo date

2019-04-30

 ISSN

1615-4150

 Source

Advanced Synthesis & Catalysis, 360, 1-7

 Part of collection

Institutional Repository

 Document type

journal article

 Rights

© 2018 F. Trausel, B. Fan, S.A.P. van Rossum, J.H. van Esch, R. Eelkema
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