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Updated: Feb 27, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Fusing Dicarbollide Ions with N-Heterocyclic Carbenes
Jess Estrada1, Vincent Lavallo1
1Department of Chemistry, University of California Riverside, Riverside, CA, 92521, USA.
Abstract:
Discovered by Hawthorne in 1965, dicarbollide ions are an intriguing class of nido-carboranes that mimic the behavior of the cyclopentadienyl anion. Herein, we show that it is possible to directly link the dicarbollide ion to an N-heterocyclic carbene (NHC) to form an isolable N-dicarbollide-substituted NHC dianion. This molecule can be accessed by the sequential double deprotonation of a mono-nido-carboranyl imidazolium zwitterion. As revealed by a single-crystal X-ray diffraction study, the first deprotonation leads to a monoanionic dicarbollide ion that adopts a bis(dicarbollide) structure in the solid state. Subsequent deprotonation of this monoanion leads to the first N-dicarbollide NHC, which was fully characterized by multinuclear NMR spectroscopy as well as single-crystal X-ray diffraction.
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