Palladium-Catalyzed Direct C2-Arylation of an N-Heterocyclic Carbene: An Atom-Economic Route to Mesoionic Carbene Ligands

Ghadwal R, Reichmann SO, Herbst-Irmer R (2015)
Chemistry - A European Journal 21(11): 4247-4251.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Ghadwal, RajendraUniBi ; Reichmann, Sven O.; Herbst-Irmer, Regine
Abstract / Bemerkung
Blocking the C2 position of an imidazole‐derived classical N‐heterocyclic carbene (NHC) with an aryl group is an essential strategy to establish a route to mesoionic carbenes (MICs), which coordinate to the metal via the C4 (or C5) carbon atom. An efficient catalytic route to MIC precursors by direct arylation of an NHC is reported. Treatment of 1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene (IPr) with an aryl iodide (RC6H4I) in the presence of 0.5 mol % of [Pd2(dba)3] (dba=dibenzylideneacetone) precatalyst affords the C2‐arylated imidazolium salts {IPr(C6H4R)}I (R=H, 4‐Me, 2‐Me, 4‐OMe, 4‐COOMe) in excellent (up to 92 %) yields. Treatment of {IPr(C6H5)}I with CuI and KN(SiMe3)2 exclusively affords the MIC–copper complex [(IPrPh)CuI].
Erscheinungsjahr
2015
Zeitschriftentitel
Chemistry - A European Journal
Band
21
Ausgabe
11
Seite(n)
4247-4251
ISSN
09476539
Page URI
https://pub.uni-bielefeld.de/record/2951031

Zitieren

Ghadwal R, Reichmann SO, Herbst-Irmer R. Palladium-Catalyzed Direct C2-Arylation of an N-Heterocyclic Carbene: An Atom-Economic Route to Mesoionic Carbene Ligands. Chemistry - A European Journal. 2015;21(11):4247-4251.
Ghadwal, R., Reichmann, S. O., & Herbst-Irmer, R. (2015). Palladium-Catalyzed Direct C2-Arylation of an N-Heterocyclic Carbene: An Atom-Economic Route to Mesoionic Carbene Ligands. Chemistry - A European Journal, 21(11), 4247-4251. https://doi.org/10.1002/chem.201405923
Ghadwal, R., Reichmann, S. O., and Herbst-Irmer, R. (2015). Palladium-Catalyzed Direct C2-Arylation of an N-Heterocyclic Carbene: An Atom-Economic Route to Mesoionic Carbene Ligands. Chemistry - A European Journal 21, 4247-4251.
Ghadwal, R., Reichmann, S.O., & Herbst-Irmer, R., 2015. Palladium-Catalyzed Direct C2-Arylation of an N-Heterocyclic Carbene: An Atom-Economic Route to Mesoionic Carbene Ligands. Chemistry - A European Journal, 21(11), p 4247-4251.
R. Ghadwal, S.O. Reichmann, and R. Herbst-Irmer, “Palladium-Catalyzed Direct C2-Arylation of an N-Heterocyclic Carbene: An Atom-Economic Route to Mesoionic Carbene Ligands”, Chemistry - A European Journal, vol. 21, 2015, pp. 4247-4251.
Ghadwal, R., Reichmann, S.O., Herbst-Irmer, R.: Palladium-Catalyzed Direct C2-Arylation of an N-Heterocyclic Carbene: An Atom-Economic Route to Mesoionic Carbene Ligands. Chemistry - A European Journal. 21, 4247-4251 (2015).
Ghadwal, Rajendra, Reichmann, Sven O., and Herbst-Irmer, Regine. “Palladium-Catalyzed Direct C2-Arylation of an N-Heterocyclic Carbene: An Atom-Economic Route to Mesoionic Carbene Ligands”. Chemistry - A European Journal 21.11 (2015): 4247-4251.

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