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Updated: Mar 25, 2026
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Comparison of boron-assisted oxime and hydrazone formations leads to the discovery of a fluorogenic variant
Cedric J Stress1, Pascal J Schmidt, Dennis G Gillingham
1Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland. dennis.gillingham@unibas.ch.
Abstract:
We use kinetic data, photophysical properties, and mechanistic analyses to compare recently developed high-rate constant oxime and hydrazone formations. We show that when Schiff base formation between aldehydes and arylhydrazines is carried out with an appropriately positioned boron atom, then aromatic B-N heterocycles form irreversibly. These consist of an extended aromatic structure amenable to the tailoring of specific properties such as reaction rate and fluorescence. The reactions work best in neutral aqueous buffer and can be designed to be fluorogenic - properties which are particularly interesting in bioconjugation.
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