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Iridium and rhodium complexes with the planar chiral thioether ligands in asymmetric hydrogenation of ketones and imines

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Abstract

Rhodium complexes with the planar chiral phosphinoferrocenyl thioether ligands [Rh(P,SR)(diene)X] (R = Me, But, Ph, Bn, diene is cyclooctadiene (COD) or norbornadiene (NBD), X = Cl, BF4) catalyze hydrogenation of ketones, imines, and heteroaromatic compounds; in the case of acetophenone, the enantioselectivity reached 60% ee. Similar iridium complexes demonstrate a good activity in the hydrogenation of imines, the maximal enantioselectivity in the case of N-phenyl-N-(1-phenylethylidene)amine was about 40% ee.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    E. M. Kozinets, G. A. Silantyev, N. V. Belkova & E. S. Shubina

  2. Laboratory of Coordination Chemistry, National Center of Scientific Studies, 205 Route de Narbonne, 31077, Toulouse, France

    E. M. Kozinets, R. Poli & E. Manoury

  3. P. Sabatier University, 205 Route de Narbonne, 31077, Toulouse, France

    E. M. Kozinets, R. Poli & E. Manoury

  4. University Institute of France, 103 bd. Saint-Michel, 75005, Paris, France

    R. Poli

Authors
  1. E. M. Kozinets
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  2. G. A. Silantyev
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  3. N. V. Belkova
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  4. E. S. Shubina
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  5. R. Poli
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  6. E. Manoury
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Correspondence to E. M. Kozinets.

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Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

Laboratoire de Chimie de Coordination, Centre National de la Recherche Scientifique, France, 31077 Toulouse, Route de Narbonne, 205.

Universite P. Sabatier, France, 31077 Toulouse, Route de Narbonne, 205.

Institut Universitaire de France, France, 75005 Paris, bd Saint-Michel, 103.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0750–0756, March, 2013.

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Kozinets, E.M., Silantyev, G.A., Belkova, N.V. et al. Iridium and rhodium complexes with the planar chiral thioether ligands in asymmetric hydrogenation of ketones and imines. Russ Chem Bull 62, 751–757 (2013). https://doi.org/10.1007/s11172-013-0102-5

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  • DOI: https://doi.org/10.1007/s11172-013-0102-5

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