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    Unusual NHC-Iridium(I) Complexes and Their Use in the Intramolecular Hydroamination of Unactivated Aminoalkenes

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    Type
    Article
    Authors
    Sipos, Gellért
    Ou, Arnold
    Skelton, Brian W.
    Falivene, Laura cc
    Cavallo, Luigi cc
    Dorta, Reto
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2016-04-10
    Online Publication Date
    2016-04-05
    Print Publication Date
    2016-05-10
    Embargo End Date
    2017-04-10
    Permanent link to this record
    http://hdl.handle.net/10754/621715
    
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    Abstract
    N-heterocyclic carbene (NHC) ligands with naphthyl side chains were employed for the synthesis of unsaturated, yet isolable [(NHC)Ir(cod)]+ (cod=1,5-cyclooctadiene) complexes. These compounds are stabilised by an interaction of the aromatic wingtip that leads to a sideways tilt of the NHC-Ir bond. Detailed studies show how the tilting of such N-heterocyclic carbenes affects the electronic shielding properties of the carbene carbon atom and how this is reflected by significant upfield shifts in the 13CNMR signals. When employed in the intramolecular hydroamination, these [(NHC)Ir(cod)]+ species show very high catalytic activity under mild reaction conditions. An enantiopure version of the catalyst system produces pyrrolidines with excellent enantioselectivities. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
    Citation
    Sipos G, Ou A, Skelton BW, Falivene L, Cavallo L, et al. (2016) Unusual NHC-Iridium(I) Complexes and Their Use in the Intramolecular Hydroamination of Unactivated Aminoalkenes. Chem Eur J 22: 6939–6946. Available: http://dx.doi.org/10.1002/chem.201600378.
    Sponsors
    G.S. thanks the UWA for an International Postgraduate Research Scholarship. R.D. thanks the Australian Research Council for generous funding (FT130101713). The Centre for Microscopy, Characterisation & Analysis at the UWA is thanked for providing facilities and assistance. L. C. thanks the King Abdullah University of Science and Technology for financial support.
    Publisher
    Wiley
    Journal
    Chemistry - A European Journal
    DOI
    10.1002/chem.201600378
    PubMed ID
    27059164
    Additional Links
    https://api.research-repository.uwa.edu.au/files/38275922/Sipos_et_al_2016Unusual_NHC_Iridium_I_.pdf
    Relations
    Is Supplemented By:
    • [Dataset]
      Sipos, G., Ou, A., Skelton, B. W., Falivene, L., Cavallo, L., & Dorta, R. (2016). CCDC 1433190: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1k3byy. DOI: 10.5517/ccdc.csd.cc1k3byy HANDLE: 10754/624530
    • [Dataset]
      Sipos, G., Ou, A., Skelton, B. W., Falivene, L., Cavallo, L., & Dorta, R. (2016). CCDC 1433191: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1k3bzz. DOI: 10.5517/ccdc.csd.cc1k3bzz HANDLE: 10754/624531
    • [Dataset]
      Sipos, G., Ou, A., Skelton, B. W., Falivene, L., Cavallo, L., & Dorta, R. (2016). CCDC 1433192: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1k3c01. DOI: 10.5517/ccdc.csd.cc1k3c01 HANDLE: 10754/624532
    • [Dataset]
      Sipos, G., Ou, A., Skelton, B. W., Falivene, L., Cavallo, L., & Dorta, R. (2016). CCDC 1433193: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1k3c12. DOI: 10.5517/ccdc.csd.cc1k3c12 HANDLE: 10754/624533
    • [Dataset]
      Sipos, G., Ou, A., Skelton, B. W., Falivene, L., Cavallo, L., & Dorta, R. (2016). CCDC 1433194: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1k3c23. DOI: 10.5517/ccdc.csd.cc1k3c23 HANDLE: 10754/624534
    • [Dataset]
      Sipos, G., Ou, A., Skelton, B. W., Falivene, L., Cavallo, L., & Dorta, R. (2016). CCDC 1433195: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1k3c34. DOI: 10.5517/ccdc.csd.cc1k3c34 HANDLE: 10754/624535
    • [Dataset]
      Sipos, G., Ou, A., Skelton, B. W., Falivene, L., Cavallo, L., & Dorta, R. (2016). CCDC 1433196: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1k3c45. DOI: 10.5517/ccdc.csd.cc1k3c45 HANDLE: 10754/624536
    ae974a485f413a2113503eed53cd6c53
    10.1002/chem.201600378
    Scopus Count
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    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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