Issue 57, 2025

Development of electronically tuneable N-heterocyclic borates

Abstract

In this contribution, we describe the synthesis and characterization of novel borates constructed with N-heterocyclic arene substituents. Beyond providing comparable electronic and redox properties to their fluoroarene analogues, the use of N-heterocycles allows for facile protonation of aromatic nitrogen atoms, thus providing a framework for tuneable reagents with varying Lewis basicity. The synthesized protonated borates were further examined as Brønstead–Lowry acids through pKa bracketing and evaluation of the kinetic accessibility of their protons by variable temperature NMR. Finally, we report the synthesis of onium and alkali metal salts of these borates through deprotonation by a variety of bases providing useful starting points for future applications.

Graphical abstract: Development of electronically tuneable N-heterocyclic borates

Supplementary files

Article information

Article type
Communication
Submitted
19 Mar 2025
Accepted
12 Jun 2025
First published
18 Jun 2025
This article is Open Access
Creative Commons BY license

Chem. Commun., 2025,61, 10610-10613

Development of electronically tuneable N-heterocyclic borates

I. J. Huerfano, E. Gorobets, W. Zhou, W. E. Piers, J. F. Van Humbeck and D. J. Derksen, Chem. Commun., 2025, 61, 10610 DOI: 10.1039/D5CC01578B

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