The Viability of C5-Protonated- and C4,C5-Ditopic Carbanionic Abnormal NHCs: A New Dimension in NHC Chemistry

Rottschäfer D, Ebeler F, Strothmann T, Neumann B, Stammler H-G, Mix A, Ghadwal R (2018)
CHEMISTRY-A EUROPEAN JOURNAL 24(15): 3716-3720.

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Abstract / Bemerkung
The first C5-protonated abnormal N-heterocyclic carbene (aNHC), PhC{N(2,6-iPr(2)C(6)H(3))}(2)CHC: (4) is readily accessible by C4-deprotonation of [ArC{N(2,6-iPr(2)C(6)H(3))}(2)CHCH]X (3a-X) (Ar=Ph, X=Br or I) with a base. The aNHC 4 is stable at 298K in [D-8]THF solution and has been spectroscopically characterized. The facile availability of 4 enables the synthesis of a series of main-group compounds as well as transition-metal complexes featuring a new phosphorus-aNHC hybrid ligand. Double deprotonation of [ArC{N(2,6-iPr(2)C(6)H(3))}(2)CHCH]X (Ar=Ph, 3a-X (X=Br or I); 4-Tol, 3b-Br; 4-DMP, 3c-Br; Tol=MeC6H4, DMP=Me2NC6H4) with nBuLi yields the C4,C5-ditopic carbanionic aNHCs, [ArC{N(2,6-iPr(2)C(6)H(3))}(2)(C:)(2)]Li(THF)(n) (Ar=Ph, 13a; 4-Tol, 13b; 4-DMP, 13c), which on treatment with Ph2PCl affords cationic vicinal bisphosphine derivatives [ArC{N(2,6-iPr(2)C(6)H(3))}(2){C(PPh2}(2)]X (Ar=Ph, 14a-X, X=Br or I; 4-Tol, 14b-Br; 4-DMP, 14c-Br).
Stichworte
carbenes; ligand design; main group; N-heterocycles; phosphorus
Erscheinungsjahr
2018
Zeitschriftentitel
CHEMISTRY-A EUROPEAN JOURNAL
Band
24
Ausgabe
15
Seite(n)
3716-3720
ISSN
0947-6539
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/2919056

Zitieren

Rottschäfer D, Ebeler F, Strothmann T, et al. The Viability of C5-Protonated- and C4,C5-Ditopic Carbanionic Abnormal NHCs: A New Dimension in NHC Chemistry. CHEMISTRY-A EUROPEAN JOURNAL. 2018;24(15):3716-3720.
Rottschäfer, D., Ebeler, F., Strothmann, T., Neumann, B., Stammler, H. - G., Mix, A., & Ghadwal, R. (2018). The Viability of C5-Protonated- and C4,C5-Ditopic Carbanionic Abnormal NHCs: A New Dimension in NHC Chemistry. CHEMISTRY-A EUROPEAN JOURNAL, 24(15), 3716-3720. doi:10.1002/chem.201800260
Rottschäfer, Dennis, Ebeler, Falk, Strothmann, Till, Neumann, Beate, Stammler, Hans-Georg, Mix, Andreas, and Ghadwal, Rajendra. 2018. “The Viability of C5-Protonated- and C4,C5-Ditopic Carbanionic Abnormal NHCs: A New Dimension in NHC Chemistry”. CHEMISTRY-A EUROPEAN JOURNAL 24 (15): 3716-3720.
Rottschäfer, D., Ebeler, F., Strothmann, T., Neumann, B., Stammler, H. - G., Mix, A., and Ghadwal, R. (2018). The Viability of C5-Protonated- and C4,C5-Ditopic Carbanionic Abnormal NHCs: A New Dimension in NHC Chemistry. CHEMISTRY-A EUROPEAN JOURNAL 24, 3716-3720.
Rottschäfer, D., et al., 2018. The Viability of C5-Protonated- and C4,C5-Ditopic Carbanionic Abnormal NHCs: A New Dimension in NHC Chemistry. CHEMISTRY-A EUROPEAN JOURNAL, 24(15), p 3716-3720.
D. Rottschäfer, et al., “The Viability of C5-Protonated- and C4,C5-Ditopic Carbanionic Abnormal NHCs: A New Dimension in NHC Chemistry”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 24, 2018, pp. 3716-3720.
Rottschäfer, D., Ebeler, F., Strothmann, T., Neumann, B., Stammler, H.-G., Mix, A., Ghadwal, R.: The Viability of C5-Protonated- and C4,C5-Ditopic Carbanionic Abnormal NHCs: A New Dimension in NHC Chemistry. CHEMISTRY-A EUROPEAN JOURNAL. 24, 3716-3720 (2018).
Rottschäfer, Dennis, Ebeler, Falk, Strothmann, Till, Neumann, Beate, Stammler, Hans-Georg, Mix, Andreas, and Ghadwal, Rajendra. “The Viability of C5-Protonated- and C4,C5-Ditopic Carbanionic Abnormal NHCs: A New Dimension in NHC Chemistry”. CHEMISTRY-A EUROPEAN JOURNAL 24.15 (2018): 3716-3720.

2 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

N-Heterocyclic Carbene Analogues of Thiele and Chichibabin Hydrocarbons.
Rottschäfer D, Ho NKT, Neumann B, Stammler HG, van Gastel M, Andrada DM, Ghadwal RS., Angew Chem Int Ed Engl 57(20), 2018
PMID: 29668119

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