Synthesis of Chiral Bifunctional NHC Ligands and Survey of Their Utilities in Asymmetric Gold Catalysis

The synthesis and characterization of the chiral bifunctional NHC ligands based on the imidazo­[1,5-a]­pyridine (ImPy) scaffold are described. These ligands possess a fluxional biaryl axis and a chiral center. The configurational stability of the biaryl axis in their gold­(I) complexes is investigat...

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Published inOrganometallics Vol. 38; no. 20; pp. 3931 - 3938
Main Authors Zhang, Jun-Qi, Liu, Yunkui, Wang, Xing-Wang, Zhang, Liming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.10.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
N-HETEROCYCLIC CARBENE
ACID
ISOMERIZATIONS
COMPLEXES
SILVER
CYCLOPROPANATION
ALKYNES
AU(I)
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Summary:The synthesis and characterization of the chiral bifunctional NHC ligands based on the imidazo­[1,5-a]­pyridine (ImPy) scaffold are described. These ligands possess a fluxional biaryl axis and a chiral center. The configurational stability of the biaryl axis in their gold­(I) complexes is investigated. The application of these axially chiral ImPy-based AuCl complexes in a series of gold catalysis is explored, and varying degrees of asymmetric induction are observed. In most cases, the ligand (aS,R)-L8-H with its cyclohexyl group pointing to the reaction site and hence exerting asymmetric steric influence is more effective in asymmetric induction.
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ISSN:0276-7333
1520-6041
DOI:10.1021/acs.organomet.9b00400