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 / Notes
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).
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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, 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.
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