Normal-to-abnormal rearrangement of an N-heterocyclic carbene with a silylene transition metal complex
Ghadwal R, Rottschäfer D, Andrada DM, Frenking G, Schuermann CJ, Stammler H-G (2017)
DALTON TRANSACTIONS 46(24): 7791-7799.
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Autor*in
Ghadwal, RajendraUniBi ;
Rottschäfer, DennisUniBi;
Andrada, Diego M.;
Frenking, Gernot;
Schuermann, Christian J.;
Stammler, Hans-GeorgUniBi
Abstract / Bemerkung
The synthesis and characterization of the N-heterocyclic carbene (NHC) stabilized dichlorosilylene Group 6 metal complexes {(IPr) SiCl2} W(CO)(5) (3-W), {(IPr) SiCl2} 2Cr(CO) 4 (4-Cr), and {(IPr) SiCl2} 2W(CO) 4 (4-W) (IPr = 1,3-bis(2,6-diisopropylphenyl) imidazol-2-ylidene) are reported. Treatment of 3-W with CsOH in the presence of IPr leads to the formation of an abnormal-NHC (aNHC) metal complex (aIPr(H)) W(CO) 5 (6-W) (aIPr(H) = 1,3-bis(2,6-diisopropylphenyl) imidazol-4-ylidene), unveiling an unprecedented normal-toabnormal transformation route of an NHC. DFT calculations support the proposed mechanism that involves CsOH mediated deprotonation of the IPr-backbone of 3-W to yield a ditopic carbanionic-NHC (dcNHC) complex 5a-W. Subsequent 1,4-migration of the W(CO)(5) moiety and hydrolysis of the unmasked SiCl2 rationalize the formation of 6-W. The desired H2O molecule is generated in the initial step on deprotonation of IPr with CsOH. In contrast to the literature precedents, the calculations indicate that the abnormal complex 6-W is 13.5 kcal mol(-1) thermodynamically higher in energy than the normal counterpart (IPr) W(CO)(5) (8-W). Interestingly, as the aNHC-compounds reported so far are more stable than their normal counterparts, this finding showcases an opposite trend. Moreover, reaction pathways to the synthesized and related complexes have been investigated by DFT calculations.
Erscheinungsjahr
2017
Zeitschriftentitel
DALTON TRANSACTIONS
Band
46
Ausgabe
24
Seite(n)
7791-7799
ISSN
1477-9226
eISSN
1477-9234
Page URI
https://pub.uni-bielefeld.de/record/2912979
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Ghadwal R, Rottschäfer D, Andrada DM, Frenking G, Schuermann CJ, Stammler H-G. Normal-to-abnormal rearrangement of an N-heterocyclic carbene with a silylene transition metal complex. DALTON TRANSACTIONS. 2017;46(24):7791-7799.
Ghadwal, R., Rottschäfer, D., Andrada, D. M., Frenking, G., Schuermann, C. J., & Stammler, H. - G. (2017). Normal-to-abnormal rearrangement of an N-heterocyclic carbene with a silylene transition metal complex. DALTON TRANSACTIONS, 46(24), 7791-7799. doi:10.1039/c7dt01199g
Ghadwal, Rajendra, Rottschäfer, Dennis, Andrada, Diego M., Frenking, Gernot, Schuermann, Christian J., and Stammler, Hans-Georg. 2017. “Normal-to-abnormal rearrangement of an N-heterocyclic carbene with a silylene transition metal complex”. DALTON TRANSACTIONS 46 (24): 7791-7799.
Ghadwal, R., Rottschäfer, D., Andrada, D. M., Frenking, G., Schuermann, C. J., and Stammler, H. - G. (2017). Normal-to-abnormal rearrangement of an N-heterocyclic carbene with a silylene transition metal complex. DALTON TRANSACTIONS 46, 7791-7799.
Ghadwal, R., et al., 2017. Normal-to-abnormal rearrangement of an N-heterocyclic carbene with a silylene transition metal complex. DALTON TRANSACTIONS, 46(24), p 7791-7799.
R. Ghadwal, et al., “Normal-to-abnormal rearrangement of an N-heterocyclic carbene with a silylene transition metal complex”, DALTON TRANSACTIONS, vol. 46, 2017, pp. 7791-7799.
Ghadwal, R., Rottschäfer, D., Andrada, D.M., Frenking, G., Schuermann, C.J., Stammler, H.-G.: Normal-to-abnormal rearrangement of an N-heterocyclic carbene with a silylene transition metal complex. DALTON TRANSACTIONS. 46, 7791-7799 (2017).
Ghadwal, Rajendra, Rottschäfer, Dennis, Andrada, Diego M., Frenking, Gernot, Schuermann, Christian J., and Stammler, Hans-Georg. “Normal-to-abnormal rearrangement of an N-heterocyclic carbene with a silylene transition metal complex”. DALTON TRANSACTIONS 46.24 (2017): 7791-7799.
Daten bereitgestellt von European Bioinformatics Institute (EBI)
5 Zitationen in Europe PMC
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