Unusual NHC-Iridium(I) Complexes and Their Use in the Intramolecular Hydroamination of Unactivated Aminoalkenes
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AbstractN-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.
CitationSipos 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.
SponsorsG.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.
JournalChemistry - A European Journal
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