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Issue 36, 2014
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Synthesis and structural investigation of R2Si (R = Me, Ph) bridged di-N-heterocyclic carbenes

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Abstract

Functionalization of the C4 carbon of an imidazol-derived N-heterocyclic carbene (NHC) may allow fine-tuning of the electronic and steric properties of the C2 carbene center. A facile route to silyl-functionalized di-N-heterocyclic carbenes (Di-NHCs) is described. Treatment of the polymeric lithiated NHC, {Li(IPrH)}n (1) (Li(IPrH) = {(N-2,6-iPr2C6H3)2CHCLi}C:) with a dichlorosilane affords monomeric silyl-functionalized Di-NHCs, R2Si(IPrH)2 (R = Ph, 2; Me, 3). Interestingly, silyl-functionalized mono-NHC, Ph2(Cl)Si(IPrH) (4) with a pendant chloro-substituent can also be exclusively isolated maintaining the reactants 1 and Ph2SiCl2 ratio. NHCs 2 and 4 readily form copper complexes, Ph2Si{(IPrH)CuCl}2 (5) and Ph2(Cl)Si{(IPrH)CuCl} (6), on reaction with CuCl. Straightforward conversion of an NHC to a Di-NHC (2 or 3) via C4 functionalization is reported for the first time. Molecular structures of 2, 4, 5 and 6 have been established by single crystal X-ray diffraction studies.

Graphical abstract: Synthesis and structural investigation of R2Si (R = Me, Ph) bridged di-N-heterocyclic carbenes

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Publication details

The article was received on 06 Jun 2014, accepted on 24 Jul 2014 and first published on 24 Jul 2014


Article type: Paper
DOI: 10.1039/C4DT01681E
Dalton Trans., 2014,43, 13704-13710
  • Open access: Creative Commons BY license
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    Synthesis and structural investigation of R2Si (R = Me, Ph) bridged di-N-heterocyclic carbenes

    R. S. Ghadwal, S. O. Reichmann, E. Carl and R. Herbst-Irmer, Dalton Trans., 2014, 43, 13704
    DOI: 10.1039/C4DT01681E

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