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Organic carbonates as alternative solvents for asymmetric hydrogenation.
Chirality. 2009 Oct; 21(9):857-61.C

Abstract

Organic carbonates like propylene carbonate (PC) or butylene carbonate (BC) belong to the class of aprotic, highly dipolar solvents (AHD). Interestingly, their potential as solvents for asymmetric catalysis has been overlooked for a long time. The aim of this work is to evaluate organic carbonates and other organic solvents like THF, CH(2)Cl(2), and acetonitrile as well as members of the AHD-family (DMF, DMSO, etc.) as media for homogeneous asymmetric hydrogenation. For this reason cationic Rh-complexes based on chiral phosphine ligands were tested in the hydrogenation of typical benchmark substrates. In several trials, significant advantages of organic carbonates were found. In contrast to DMSO, DMF and acetonitrile, in PC and BC high conversion rates and excellent enantioselectivities were usually observed.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Schäffner B
Leibniz-Institut für Katalyse an der Universität Rostock e.V., Rostock 18059, Germany.
Andrushko V
No affiliation info available
Bayardon J
No affiliation info available
Holz J
No affiliation info available
Börner A
No affiliation info available

MeSH

Carbonic AcidCatalysisGreen Chemistry TechnologyHydrogenationOrganic ChemicalsRhodiumSolventsStereoisomerismSubstrate Specificity

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19455615

Citation

Schäffner, Benjamin, et al. "Organic Carbonates as Alternative Solvents for Asymmetric Hydrogenation." Chirality, vol. 21, no. 9, 2009, pp. 857-61.
Schäffner B, Andrushko V, Bayardon J, et al. Organic carbonates as alternative solvents for asymmetric hydrogenation. Chirality. 2009;21(9):857-61.
Schäffner, B., Andrushko, V., Bayardon, J., Holz, J., & Börner, A. (2009). Organic carbonates as alternative solvents for asymmetric hydrogenation. Chirality, 21(9), 857-61. https://doi.org/10.1002/chir.20720
Schäffner B, et al. Organic Carbonates as Alternative Solvents for Asymmetric Hydrogenation. Chirality. 2009;21(9):857-61. PubMed PMID: 19455615.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Organic carbonates as alternative solvents for asymmetric hydrogenation. AU - Schäffner,Benjamin, AU - Andrushko,Vasyl, AU - Bayardon,Jerome, AU - Holz,Jens, AU - Börner,Armin, PY - 2009/5/21/entrez PY - 2009/5/21/pubmed PY - 2009/12/30/medline SP - 857 EP - 61 JF - Chirality JO - Chirality VL - 21 IS - 9 N2 - Organic carbonates like propylene carbonate (PC) or butylene carbonate (BC) belong to the class of aprotic, highly dipolar solvents (AHD). Interestingly, their potential as solvents for asymmetric catalysis has been overlooked for a long time. The aim of this work is to evaluate organic carbonates and other organic solvents like THF, CH(2)Cl(2), and acetonitrile as well as members of the AHD-family (DMF, DMSO, etc.) as media for homogeneous asymmetric hydrogenation. For this reason cationic Rh-complexes based on chiral phosphine ligands were tested in the hydrogenation of typical benchmark substrates. In several trials, significant advantages of organic carbonates were found. In contrast to DMSO, DMF and acetonitrile, in PC and BC high conversion rates and excellent enantioselectivities were usually observed. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/19455615/Organic_carbonates_as_alternative_solvents_for_asymmetric_hydrogenation_ L2 - https://doi.org/10.1002/chir.20720 DB - PRIME DP - Unbound Medicine ER -