Synthesis and structural investigation of R Si (R = Me, Ph) bridged di-N-heterocyclic carbenes

Ghadwal R, Reichmann SO, Carl E, Herbst-Irmer R (2014)
Dalton Trans. 43(36): 13704-13710.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Ghadwal, RajendraUniBi ; Reichmann, Sven O.; Carl, Elena; Herbst-Irmer, Regine
Abstract / Bemerkung
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.
Erscheinungsjahr
2014
Zeitschriftentitel
Dalton Trans.
Band
43
Ausgabe
36
Seite(n)
13704-13710
ISSN
1477-9226
eISSN
1477-9234
Page URI
https://pub.uni-bielefeld.de/record/2951032

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Ghadwal R, Reichmann SO, Carl E, Herbst-Irmer R. Synthesis and structural investigation of R Si (R = Me, Ph) bridged di-N-heterocyclic carbenes. Dalton Trans. 2014;43(36):13704-13710.
Ghadwal, R., Reichmann, S. O., Carl, E., & Herbst-Irmer, R. (2014). Synthesis and structural investigation of R Si (R = Me, Ph) bridged di-N-heterocyclic carbenes. Dalton Trans., 43(36), 13704-13710. https://doi.org/10.1039/C4DT01681E
Ghadwal, R., Reichmann, S. O., Carl, E., and Herbst-Irmer, R. (2014). Synthesis and structural investigation of R Si (R = Me, Ph) bridged di-N-heterocyclic carbenes. Dalton Trans. 43, 13704-13710.
Ghadwal, R., et al., 2014. Synthesis and structural investigation of R Si (R = Me, Ph) bridged di-N-heterocyclic carbenes. Dalton Trans., 43(36), p 13704-13710.
R. Ghadwal, et al., “Synthesis and structural investigation of R Si (R = Me, Ph) bridged di-N-heterocyclic carbenes”, Dalton Trans., vol. 43, 2014, pp. 13704-13710.
Ghadwal, R., Reichmann, S.O., Carl, E., Herbst-Irmer, R.: Synthesis and structural investigation of R Si (R = Me, Ph) bridged di-N-heterocyclic carbenes. Dalton Trans. 43, 13704-13710 (2014).
Ghadwal, Rajendra, Reichmann, Sven O., Carl, Elena, and Herbst-Irmer, Regine. “Synthesis and structural investigation of R Si (R = Me, Ph) bridged di-N-heterocyclic carbenes”. Dalton Trans. 43.36 (2014): 13704-13710.

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