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PreprintCC BY-NC-NDChemRxiv

Synthesis and Ambiphilic Reactivity of a Monocoordinate Carbazolyl Gallylene

  • Nasrina Parvin1
  • T. Ilgin Demirer1
  • Dennis Welterlich1,2
  • Bernd Morgenstern1
  • Alexander Hinz3
  • Diego M. Andrada1
  1. 1Department of Chemistry, Faculty of Natural Sciences and Technology, Saarland University, Campus C4.1, Saarbrücken, Germany, 66123
  2. 2Institute of Inorganic Chemistry and Institute for Sustainable Chemistry and Catalysis with Boron Julius-Maximilians-Universität Würzburg
  3. 3Department for Chemistry, Institute for Inorganic and Analytical Chemistry, Friedrich-Schiller-Universität Jena, Humboldtstraße 8, Jena, Germany, 07743
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Abstract

Monocoordinate Lewis base-free gallium(I) complexes are rare due to their high propensity for disproportionation and oligomerization. Herein, we report the synthesis and structural characterization of a monomeric, monocoordinate gallylene stabilized by a bulky 1,8-bis(3,5-ditert-butylphenyl)-3,6-di-tert-butylcarbazole ligand. Taking advantage of the substantial kinetic shielding provided by the flanking aryl substituents, the compound can be isolated as a solvent free, one-coordinate main-group carbenoid. With a lone pair and two vacant p-orbitals, this compound features an ambiphilic character which was experimentally probed through coordination to both Lewis-acidic transition-metal fragments (M(CO) 5 ; M = Cr, Mo, W) and strong σ-donor Lewis bases, including the N-heterocyclic carbene ( IPrMe NHC) and 4-dimethylaminopyridine (DMAP). Furthermore, the Ga(I) complex shows oxidative addition of methyl iodide and phenanthrene-9,10-dione. Conversely to other monocoordinate gallylene compounds its carbometallation reactions are kinetically and thermodynamically unfavored.

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Cite

BibTeXRIS
BibTeX
@misc{parvin2026synthesis,
  title = {{Synthesis and Ambiphilic Reactivity of a Monocoordinate Carbazolyl Gallylene}},
  author = {Nasrina Parvin and T. Ilgin Demirer and Dennis Welterlich and Bernd Morgenstern and Alexander Hinz and Diego M. Andrada},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15009153/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009153/v1},
  note = {CC BY-NC-ND},
}
RIS
TY  - UNPB
TI  - Synthesis and Ambiphilic Reactivity of a Monocoordinate Carbazolyl Gallylene
AU  - Nasrina Parvin
AU  - T. Ilgin Demirer
AU  - Dennis Welterlich
AU  - Bernd Morgenstern
AU  - Alexander Hinz
AU  - Diego M. Andrada
PY  - 2026
DA  - 2026/09/21
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15009153/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15009153/v1
AB  - Monocoordinate Lewis base-free gallium(I) complexes are rare due to their high propensity for disproportionation and oligomerization. Herein, we report the synthesis and structural characterization of a monomeric, monocoordinate gallylene stabilized by a bulky 1,8-bis(3,5-ditert-butylphenyl)-3,6-di-tert-butylcarbazole ligand. Taking advantage of the substantial kinetic shielding provided by the flanking aryl substituents, the compound can be isolated as a solvent free, one-coordinate main-group carbenoid. With a lone pair and two vacant p-orbitals, this compound features an ambiphilic character which was experimentally probed through coordination to both Lewis-acidic transition-metal fragments (M(CO) 5 ; M = Cr, Mo, W) and strong σ-donor Lewis bases, including the N-heterocyclic carbene ( IPrMe NHC) and 4-dimethylaminopyridine (DMAP). Furthermore, the Ga(I) complex shows oxidative addition of methyl iodide and phenanthrene-9,10-dione. Conversely to other monocoordinate gallylene compounds its carbometallation reactions are kinetically and thermodynamically unfavored.
ER  -