Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes

Type
Article
Authors
Queval, Pierre
Jahier, Claire
Rouen, Mathieu
Artur, Isabelle
Legeay, Jean Christophe
Falivene, Laura cc
Toupet, Loïc J.
Crévisy, Christophe
Cavallo, Luigi cc
Baslé, Olivier
Mauduit, Marc
KAUST Department
Chemical Science Program
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2013-12-04
Online Publication Date
2013-12-04
Print Publication Date
2013-12-23
Permanent link to this record
http://hdl.handle.net/10754/563141

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Abstract
A low-cost, modular, and easily scalable multicomponent procedure affording access in good yields and excellent selectivity (up to 93 %) to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl-imidazolium salts is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron donor ability, high steric discrimination, and modular steric demand. A low-cost, modular, and easily scalable multicomponent procedure, affording access to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl- imidazolium salts in good yields and excellent selectivities, is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron-donor ability, high steric discrimination, and modular steric demand. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Citation
Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2013). Multicomponent Synthesis of Unsymmetrical Unsaturated N-Heterocyclic Carbene Precursors and Their Related Transition-Metal Complexes. Angewandte Chemie International Edition, 52(52), 14103–14107. doi:10.1002/anie.201308873
Publisher
Wiley
Journal
Angewandte Chemie
DOI
10.1002/anie.201308873
Relations
Is Supplemented By:
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 959340: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1168gz. DOI: 10.5517/cc1168gz HANDLE: 10754/624259
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 961393: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc118dpd. DOI: 10.5517/cc118dpd HANDLE: 10754/624261
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 961639: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc118nml. DOI: 10.5517/cc118nml HANDLE: 10754/624262
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 927645: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10491h. DOI: 10.5517/cc10491h HANDLE: 10754/624194
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 929979: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc106qb8. DOI: 10.5517/cc106qb8 HANDLE: 10754/624199
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 930139: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc106whl. DOI: 10.5517/cc106whl HANDLE: 10754/624200
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 862360: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccxyc28. DOI: 10.5517/ccxyc28 HANDLE: 10754/624672
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 862361: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccxyc39. DOI: 10.5517/ccxyc39 HANDLE: 10754/624673
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 932347: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1095q6. DOI: 10.5517/cc1095q6 HANDLE: 10754/624203
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 901079: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccz7n2x. DOI: 10.5517/ccz7n2x HANDLE: 10754/624752
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 901330: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccz7x58. DOI: 10.5517/ccz7x58 HANDLE: 10754/624753
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 904639: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cczcbxk. DOI: 10.5517/cczcbxk HANDLE: 10754/624754
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 921286: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cczxnxf. DOI: 10.5517/cczxnxf HANDLE: 10754/624767
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 867551: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccy3rj9. DOI: 10.5517/ccy3rj9 HANDLE: 10754/624684
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 933067: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc109xy5. DOI: 10.5517/cc109xy5 HANDLE: 10754/624204
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 933273: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10b4l2. DOI: 10.5517/cc10b4l2 HANDLE: 10754/624211
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 933498: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10bcvk. DOI: 10.5517/cc10bcvk HANDLE: 10754/624212
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 935381: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10dblb. DOI: 10.5517/cc10dblb HANDLE: 10754/624215
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 936702: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10fq6c. DOI: 10.5517/cc10fq6c HANDLE: 10754/624216
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 938918: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10j0p7. DOI: 10.5517/cc10j0p7 HANDLE: 10754/624218
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 939289: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10jdnl. DOI: 10.5517/cc10jdnl HANDLE: 10754/624219
  • [Dataset]
    Queval, P., Jahier, C., Rouen, M., Artur, I., Legeay, J.-C., Falivene, L., … Mauduit, M. (2014). CCDC 945381: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10qr5n. DOI: 10.5517/cc10qr5n HANDLE: 10754/624235
Collections
Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)