Nickel Catalyzed Intramolecular 1,2-Aryl Migration of Mesoionic Carbenes (iMICs)

Ghadwal, Rajendra; Merschel, Arne; Glodde, Timo; Neumann, Beate; Stammler, Hans-Georg

Nickel Catalyzed Intramolecular 1,2-Aryl Migration of Mesoionic Carbenes (iMICs)

Ghadwal R, Merschel A, Glodde T, Neumann B, Stammler H-G (2020)
Angewandte Chemie International Edition 60: 2969 –2973.

Zeitschriftenaufsatz | Veröffentlicht | Englisch

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Angew Chem Int Ed - 2020 - Merschel - Nickel_u2010Catalyzed Intramolecular 1 2_u2010Aryl Migration of Mesoionic Carbenes iMICs.pdf 1.30 MB

DOI

https://doi.org/10.1002/anie.202014328

URN

urn:nbn:de:0070-pub-29487505

Autor*in

Ghadwal, Rajendra^UniBi ; Merschel, Arne; Glodde, Timo^UniBi; Neumann, Beate^UniBi; Stammler, Hans-Georg^UniBi

Einrichtung

Fakultät für Chemie > Anorganische Chemie und Strukturchemie

Abstract / Bemerkung

Intramolecular 1,2-Dipp migration of seven meso-ionic carbenes (iMICAr)2a–g(iMICAr=ArC{N-(Dipp)}2CHC; Ar=aryl; Dipp=2,6-iPr2C6H3) under nickelcatalysis to give 1,3-imidazoles (IMDAr)3a–g(IMDAr=ArC-{N(Dipp)CHC(Dipp)N}) has been reported. The formation of3indicates the cleavage of an NCDippbond and the subsequentformation of a CCDippbond in2, which is unprecedented inNHC chemistry. The use of3in accessing super-iMICs (5) (S-iMIC=ArC{N(Dipp)N(Me)C(Dipp)}C) has been shown withselenium (6), gold (7), and palladium (8) compounds. The quantification of the stereoelectronic properties reveals thesuperiors-donor strength of5compared to that of classicalNHCs. Remarkably, the percentage buried volume of5(%Vbur=45) is the largest known amongst thus far reportediMICs. Catalytic studies show a remarkable activity of5, whichis consistent with their auspicious stereoelectronic features

Erscheinungsjahr

2020

Zeitschriftentitel

Angewandte Chemie International Edition

Band

Seite(n)

2969 –2973

Urheberrecht / Lizenzen

Creative Commons Namensnennung-Nicht kommerziell 4.0 International (CC BY-NC 4.0)

eISSN

1521-3773

Finanzierungs-Informationen

Open-Access-Publikationskosten wurden durch die Universität Bielefeld im Rahmen des DEAL-Vertrags gefördert.

Page URI

https://pub.uni-bielefeld.de/record/2948750

Zitieren

Ghadwal R, Merschel A, Glodde T, Neumann B, Stammler H-G. Nickel Catalyzed Intramolecular 1,2-Aryl Migration of Mesoionic Carbenes (iMICs). Angewandte Chemie International Edition. 2020;60:2969 –2973.

Ghadwal, R., Merschel, A., Glodde, T., Neumann, B., & Stammler, H. - G. (2020). Nickel Catalyzed Intramolecular 1,2-Aryl Migration of Mesoionic Carbenes (iMICs). Angewandte Chemie International Edition, 60, 2969 –2973. https://doi.org/10.1002/anie.202014328

Ghadwal, Rajendra, Merschel, Arne, Glodde, Timo, Neumann, Beate, and Stammler, Hans-Georg. 2020. “Nickel Catalyzed Intramolecular 1,2-Aryl Migration of Mesoionic Carbenes (iMICs)”. Angewandte Chemie International Edition 60: 2969 –2973.

Ghadwal, R., Merschel, A., Glodde, T., Neumann, B., and Stammler, H. - G. (2020). Nickel Catalyzed Intramolecular 1,2-Aryl Migration of Mesoionic Carbenes (iMICs). Angewandte Chemie International Edition 60, 2969 –2973.

Ghadwal, R., et al., 2020. Nickel Catalyzed Intramolecular 1,2-Aryl Migration of Mesoionic Carbenes (iMICs). Angewandte Chemie International Edition, 60, p 2969 –2973.

R. Ghadwal, et al., “Nickel Catalyzed Intramolecular 1,2-Aryl Migration of Mesoionic Carbenes (iMICs)”, Angewandte Chemie International Edition, vol. 60, 2020, pp. 2969 –2973.

Ghadwal, R., Merschel, A., Glodde, T., Neumann, B., Stammler, H.-G.: Nickel Catalyzed Intramolecular 1,2-Aryl Migration of Mesoionic Carbenes (iMICs). Angewandte Chemie International Edition. 60, 2969 –2973 (2020).

Ghadwal, Rajendra, Merschel, Arne, Glodde, Timo, Neumann, Beate, and Stammler, Hans-Georg. “Nickel Catalyzed Intramolecular 1,2-Aryl Migration of Mesoionic Carbenes (iMICs)”. Angewandte Chemie International Edition 60 (2020): 2969 –2973.

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