Chiral PEPPSI Complexes: Synthesis, Characterization, and Application in Asymmetric Suzuki–Miyaura Coupling Reactions

Type
Article

Authors
Benhamou, Laure
Besnard, Céline
Kündig, E. Peter

Online Publication Date
2013-12-16

Print Publication Date
2014-01-13

Date
2013-12-16

Abstract
PEPPSI complexes incorporating chiral N-heterocyclic carbene (NHC) ligands based on 2,2-dimethyl-1-(o-substituted aryl)propan-1-amines were synthesized. Two complexes, with one saturated and one unsaturated NHC ligand, were structurally characterized. The chiral PEPPSI complexes were used in asymmetric Suzuki-Miyaura reactions, giving atropisomeric biaryl products in modest to good enantiomeric ratios. © 2013 American Chemical Society.

Citation
Benhamou L, Besnard C, Kündig EP (2014) Chiral PEPPSI Complexes: Synthesis, Characterization, and Application in Asymmetric Suzuki–Miyaura Coupling Reactions. Organometallics 33: 260–266. Available: http://dx.doi.org/10.1021/om4009982.

Acknowledgements
We thank the Swiss National Science Foundation and the University of Geneva for financial support, Stephane Rosset and Prof. Alexandre Alexakis (Geneva) for the use of their supercritical fluid chromatography (SFC) equipment, and Prof. Luigi Cavallo (Salerno and KAUST) for advice on the calculation of %Vbur.

Publisher
American Chemical Society (ACS)

Journal
Organometallics

DOI
10.1021/om4009982

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