An Anionic Mesoionic Carbene (anMIC) and its Transformation to Metallo MIC‐Boranes: Synthesis and Properties

Abstract: Neutral mesoionic carbenes (MICs) based on a 1,2,3‐triazole core have had a strong impact on various branches of chemistry such as homogeneous catalysis, electrocatalysis, and photochemistry/photophysics. We present here the first general synthesis of anionic mesoionic carbenes (anMICs, 2) based on a 1,2,3‐triazole core and a borate backbone. The free anMIC is stable in solution under an inert atmosphere at low temperatures, and can be stored for several weeks. Analysis of donor properties shows that these anMICs are extremely strong σ‐donors, bypassing the donor properties of strong donors such as MICs, NHCs, anionic NHCs and N‐heterocyclic olefins. The room temperature conversion of the free anMICs leads to three equally interesting compound classes: an amide‐coordinated borane based on a MIC‐borane backbone (2BR3), a polymeric triazolide (1Li) and an amide‐coordinated metallo‐MIC‐borane. The metallo‐MIC‐borane (3Li) is an interesting precursor for the synthesis of further amide‐coordinated MIC‐borane compounds. Quantum chemical calculations have been used to elucidate the mechanism of transformation of the anMICs. We thus introduce three new categories of mesoionic compounds here with potential for different branches of chemistry and beyond.

Standort
Deutsche Nationalbibliothek Frankfurt am Main
Umfang
Online-Ressource
Sprache
Englisch

Erschienen in
An Anionic Mesoionic Carbene (anMIC) and its Transformation to Metallo MIC‐Boranes: Synthesis and Properties ; day:05 ; month:02 ; year:2025 ; extent:15
Angewandte Chemie / International edition. International edition ; (05.02.2025) (gesamt 15)

Urheber
Rudolf, Richard
Todorovski, Andrej
Lederer, Vera
Neuman, Nicolás I.
Schubert, Hartmut
Sarkar, Biprajit

DOI
10.1002/anie.202422702
URN
urn:nbn:de:101:1-2502061315530.502121213990
Rechteinformation
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Letzte Aktualisierung
15.08.2025, 07:33 MESZ

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Beteiligte

  • Rudolf, Richard
  • Todorovski, Andrej
  • Lederer, Vera
  • Neuman, Nicolás I.
  • Schubert, Hartmut
  • Sarkar, Biprajit

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