Expedient Access to Normal- and Abnormal- N-Heterocyclic Carbene (NHC) Magnesium Compounds from Imidazolium Salts

Ghadwal R, Rottschaefer D, Schuermann CJ (2016)
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE 642(22): 1236-1240.

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Treatment of imidazolium salts (IPrH)Cl (1) and (IPrH)I (2) with MeMgI leads to the formation of normal N-heterocyclic carbene (nNHC) compounds (IPr)MgCl(I) (3) and (IPr)MgI2 (4) [IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], respectively. By employing a similar strategy, the first magnesium compound (aIPr(Ph))MgI2(OEt2) (6) featuring an abnormal-NHC [aIPr(Ph) = 1,3-bis(2,6-diisopropylphenyl)-2-phenyl-imidazol-4-ylidene] is prepared by the treatment of a C2-arylated imidazolium salt (IPrPh)I (5) with MeMgI. While the deprotonation of 1 and 2 can be accomplished at room temperature, an elevated temperature is required to deprotonate 5 with MeMgI. This is most likely due to the higher pK(a) value of the C4-H than that of the C2-H hydrogen atom. Salt metathesis reaction of 6 with KN(SiMe3)(2) cleanly leads to the formation of a magnesium amide derivative (aIPr(Ph))Mg{N(SiMe3)(2)}(2) (7). Compounds 3, 4, 6, and 7 were characterized by elemental analyses and NMR spectroscopic studies. The molecular structures of 3, 4, and 6 were determined by single-crystal X-ray diffraction analyses.
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Ghadwal R, Rottschaefer D, Schuermann CJ. Expedient Access to Normal- and Abnormal- N-Heterocyclic Carbene (NHC) Magnesium Compounds from Imidazolium Salts. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE. 2016;642(22):1236-1240.
Ghadwal, R., Rottschaefer, D., & Schuermann, C. J. (2016). Expedient Access to Normal- and Abnormal- N-Heterocyclic Carbene (NHC) Magnesium Compounds from Imidazolium Salts. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 642(22), 1236-1240. doi:10.1002/zaac.201600308
Ghadwal, R., Rottschaefer, D., and Schuermann, C. J. (2016). Expedient Access to Normal- and Abnormal- N-Heterocyclic Carbene (NHC) Magnesium Compounds from Imidazolium Salts. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE 642, 1236-1240.
Ghadwal, R., Rottschaefer, D., & Schuermann, C.J., 2016. Expedient Access to Normal- and Abnormal- N-Heterocyclic Carbene (NHC) Magnesium Compounds from Imidazolium Salts. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 642(22), p 1236-1240.
R. Ghadwal, D. Rottschaefer, and C.J. Schuermann, “Expedient Access to Normal- and Abnormal- N-Heterocyclic Carbene (NHC) Magnesium Compounds from Imidazolium Salts”, ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, vol. 642, 2016, pp. 1236-1240.
Ghadwal, R., Rottschaefer, D., Schuermann, C.J.: Expedient Access to Normal- and Abnormal- N-Heterocyclic Carbene (NHC) Magnesium Compounds from Imidazolium Salts. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE. 642, 1236-1240 (2016).
Ghadwal, Rajendra, Rottschaefer, Dennis, and Schuermann, Christian J. “Expedient Access to Normal- and Abnormal- N-Heterocyclic Carbene (NHC) Magnesium Compounds from Imidazolium Salts”. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE 642.22 (2016): 1236-1240.
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