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

Laure Benhamou; Céline Besnard; E. Peter Kündig

doi:10.1021/om4009982

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

Laure Benhamou, Céline Besnard, E. Peter Kündig

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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.

Original language	English (US)
Pages (from-to)	260-266
Number of pages	7
Journal	Organometallics
Volume	33
Issue number	1
DOIs	https://doi.org/10.1021/om4009982
State	Published - Dec 16 2013
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
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.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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

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. {\textcopyright} 2013 American Chemical Society.",

author = "Laure Benhamou and C{\'e}line Besnard and K{\"u}ndig, {E. Peter}",

note = "KAUST Repository Item: Exported on 2020-10-01 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

year = "2013",

month = dec,

day = "16",

doi = "10.1021/om4009982",

language = "English (US)",

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T1 - Chiral PEPPSI Complexes: Synthesis, Characterization, and Application in Asymmetric Suzuki–Miyaura Coupling Reactions

AU - Benhamou, Laure

AU - Besnard, Céline

AU - Kündig, E. Peter

N1 - KAUST Repository Item: Exported on 2020-10-01 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. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2013/12/16

Y1 - 2013/12/16

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/597774

UR - https://pubs.acs.org/doi/10.1021/om4009982

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DO - 10.1021/om4009982

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JO - Organometallics

JF - Organometallics

IS - 1

ER -

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

Abstract

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