期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 20, 页码 6939-6946出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600378
关键词
carbenes; density functional calculations; hydroamination; heterocycles; iridium
资金
- UWA
- Australian Research Council [FT130101713]
- King Abdullah University of Science and Technology
- Australian Research Council [FT130101713] Funding Source: Australian Research Council
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 (CNMR)-C-13 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.
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