Six-Membered N-Heterocyclic Carbenes with a 1,1′-Ferrocenediyl Backbone : Bulky Ligands with Strong Electron-Donor Capacity and Unusual Non-Innocent Character

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2009
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Siemeling, Ulrich
Färber, Christian
Leibold, Michael
Bruhn, Clemens
Sarkar, Biprajit
von Hopffgarten, Moritz
Frenking, Gernod
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European Journal of Inorganic Chemistry. 2009, 2009(31), pp. 4607-4612. ISSN 1434-1948. Available under: doi: 10.1002/ejic.200900863
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Abstract

The stable, crystalline N-heterocyclic diaminocarbene fc[N(CH2tBu)-C-N(CH2tBu)] (2d, fc = 1,1′-ferrocenediyl) was prepared by deprotonation of its formamidinium precursor fc[N(CH2tBu)-CH-N(CH2tBu)][BF4] (1d) and used for the preparation of the 16 valence electron complexes [Mo(2d)(CO)4], [RhCl(2d)(cod)] (cod = 1,5-cyclooctadiene) and [RhCl(2d)(CO)2]. 1d, 2d and [RhCl(2d)(cod)] were structurally characterised by single-crystal X-ray diffraction studies. The electrochemical properties of 2d, its 2-adamantyl analogue 2c, its complex [RhCl(2d)(CO)2] and of the precursors 1d and 1,1′-bis(neopentylamino)ferrocene were investigated by electrochemistry. The carbenes are easily oxidised to the corresponding radical cation, whose persistent nature is unprecedented in the chemistry of N-heterocyclic carbenes. The spin density is located at the Fe atom and the carbene C atom according to the results of EPR spectroscopic studies and DFT calculations.

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ISO 690SIEMELING, Ulrich, Christian FÄRBER, Michael LEIBOLD, Clemens BRUHN, Philipp MÜCKE, Rainer F. WINTER, Biprajit SARKAR, Moritz VON HOPFFGARTEN, Gernod FRENKING, 2009. Six-Membered N-Heterocyclic Carbenes with a 1,1′-Ferrocenediyl Backbone : Bulky Ligands with Strong Electron-Donor Capacity and Unusual Non-Innocent Character. In: European Journal of Inorganic Chemistry. 2009, 2009(31), pp. 4607-4612. ISSN 1434-1948. Available under: doi: 10.1002/ejic.200900863
BibTex
@article{Siemeling2009SixMe-13792,
  year={2009},
  doi={10.1002/ejic.200900863},
  title={Six-Membered N-Heterocyclic Carbenes with a 1,1′-Ferrocenediyl Backbone : Bulky Ligands with Strong Electron-Donor Capacity and Unusual Non-Innocent Character},
  number={31},
  volume={2009},
  issn={1434-1948},
  journal={European Journal of Inorganic Chemistry},
  pages={4607--4612},
  author={Siemeling, Ulrich and Färber, Christian and Leibold, Michael and Bruhn, Clemens and Mücke, Philipp and Winter, Rainer F. and Sarkar, Biprajit and von Hopffgarten, Moritz and Frenking, Gernod}
}
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