Development of chiral C2-symmetric N-heterocyclic carbene Rh(I) catalysts through control of their steric properties
Chiral square-planar Rh(I) complexes based on new C2-symmetric NHC ligands have been synthesized selectively in a few steps as single diastereoisomers. These chiral pre-catalysts were applied to the asymmetric transfer hydrogenation of 1-phe-nylpropanone and to the 1,2-addition of arylboronic acids...
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Veröffentlicht in: | Organometallics 2019-01, Vol.38 (2), p.536-543 |
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Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Chiral square-planar Rh(I) complexes based on new C2-symmetric NHC ligands have been synthesized selectively in a few steps as single diastereoisomers. These chiral pre-catalysts were applied to the asymmetric transfer hydrogenation of 1-phe-nylpropanone and to the 1,2-addition of arylboronic acids to aldehydes. We demonstrated a proper functionalization of the aromatic rings connected to the nitrogen atoms of the NHC ligand improved significantly the asymmetric induction of the chiral Rh(I) NHC catalysts. Bulky substituents allowed a better control of the steric features of the catalyst quadrants because they behaved as confor-mational and chirality relays of the NHC chiral backbone. |
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ISSN: | 0276-7333 1520-6041 |
DOI: | 10.1021/acs.organomet.8b00823 |