Synthesis and characterization of chiral mono N-heterocyclic carbene-substituted rhodium complexes and their catalytic properties in hydrosilylation reactions

Steinbeck M, Frey GD, Schoeller W, Herrmann WA (2011)
Journal of Organometallic Chemistry 696(25): 3945-3954.

Journal Article | Published | English

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Abstract
Different chiral mono-substituted N-heterocyclic carbene complexes of rhodium were prepared, starting from [Rh(COD)Cl](2) (COD = cyclooctadiene) by addition of free N-heterocyclic carbenes (NHC), or an in-situ deprotonation of the corresponding iminium salt. All new complexes were characterized by spectroscopy methods. In addition, the structures of chloro(eta(4)-1,5-cyclooctadiene)(1,3-di-[(1R,2R,3R,5S)-2,6,6- trimethylbicyclo[3.1.1]hept-3-yl] imidazolin-2-ylidene) rhodium(I) (5a), chloro(eta(4)-1,5-cyclooctadiene)(1,3-di-[(1R,2S,5R)-2-isopropyl-5-menth ylcyclohex-1-yl] imidazol-2-ylidene)rhodium(I) (5b) and chloro(eta(4)-1,5-cyclooctadiene)(1,3-di-[(2R,4S,5S)-2-methyl-4-phenyl-1 ,3-dioxacyclohex-5-yl]imidazolin-2- ylidene)rhodium(I) (5i) were analyzed by DFT-calculations. The enantioselective hydrosilylation of acetophenone, ethylpyruvate and n-propylpyruvate with diphenylsilane and hydrolysis was carried out with chiral C(2)-symmetrical mono-substituted N-heterocyclic carbene rhodium complexes giving for the first time an enantioselective excess of up to 74% ee in the case of the n-propylpyruvate. (C) 2011 Elsevier B.V. All rights reserved.
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Steinbeck M, Frey GD, Schoeller W, Herrmann WA. Synthesis and characterization of chiral mono N-heterocyclic carbene-substituted rhodium complexes and their catalytic properties in hydrosilylation reactions. Journal of Organometallic Chemistry. 2011;696(25):3945-3954.
Steinbeck, M., Frey, G. D., Schoeller, W., & Herrmann, W. A. (2011). Synthesis and characterization of chiral mono N-heterocyclic carbene-substituted rhodium complexes and their catalytic properties in hydrosilylation reactions. Journal of Organometallic Chemistry, 696(25), 3945-3954.
Steinbeck, M., Frey, G. D., Schoeller, W., and Herrmann, W. A. (2011). Synthesis and characterization of chiral mono N-heterocyclic carbene-substituted rhodium complexes and their catalytic properties in hydrosilylation reactions. Journal of Organometallic Chemistry 696, 3945-3954.
Steinbeck, M., et al., 2011. Synthesis and characterization of chiral mono N-heterocyclic carbene-substituted rhodium complexes and their catalytic properties in hydrosilylation reactions. Journal of Organometallic Chemistry, 696(25), p 3945-3954.
M. Steinbeck, et al., “Synthesis and characterization of chiral mono N-heterocyclic carbene-substituted rhodium complexes and their catalytic properties in hydrosilylation reactions”, Journal of Organometallic Chemistry, vol. 696, 2011, pp. 3945-3954.
Steinbeck, M., Frey, G.D., Schoeller, W., Herrmann, W.A.: Synthesis and characterization of chiral mono N-heterocyclic carbene-substituted rhodium complexes and their catalytic properties in hydrosilylation reactions. Journal of Organometallic Chemistry. 696, 3945-3954 (2011).
Steinbeck, Martin, Frey, Guido D., Schoeller, Wolfgang, and Herrmann, Wolfgang A. “Synthesis and characterization of chiral mono N-heterocyclic carbene-substituted rhodium complexes and their catalytic properties in hydrosilylation reactions”. Journal of Organometallic Chemistry 696.25 (2011): 3945-3954.
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