Mechanistic Insights into a Supramolecular Self-Assembling Catalyst System: Evidence for Hydrogen Bonding during Rhodium-Catalyzed Hydroformylation

The structural integrity and flexibility provided by intermolecular hydrogen bonds leads to the outstanding properties of the 6‐diphenylphosphinopyridin‐(2H)‐1‐one ligand (see scheme) in the rhodium‐catalyzed hydroformylation of terminal alkenes, as demonstrated by the combination of spectroscopic m...

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Published inAngewandte Chemie (International ed.) Vol. 51; no. 44; pp. 11033 - 11038
Main Authors Gellrich, Urs, Seiche, Wolfgang, Keller, Manfred, Breit, Bernhard
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 29.10.2012
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Aldehydes - chemical synthesis
Aldehydes - chemistry
Alkenes
Alkenes - chemistry
Catalysis
Catalysts
Crystallography, X-Ray
DFT calculations
Flexibility
hydroformylation
Hydrogen Bonding
Hydrogen bonds
IR spectroscopy
Ligands
Macromolecular Substances - chemical synthesis
Macromolecular Substances - chemistry
Models, Molecular
Molecular Structure
Quantum Theory
Rhodium - chemistry
self-assembly
Spectroscopy
Stereoisomerism
Terminals
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Summary:The structural integrity and flexibility provided by intermolecular hydrogen bonds leads to the outstanding properties of the 6‐diphenylphosphinopyridin‐(2H)‐1‐one ligand (see scheme) in the rhodium‐catalyzed hydroformylation of terminal alkenes, as demonstrated by the combination of spectroscopic methods and DFT computations. Hydrogen bonds were also detected in a competent intermediate of the catalytic cycle.
Bibliography:istex:AFBF1EC1785E24F3811CC60DAA0486925DF8A856
ark:/67375/WNG-PRD5QKDK-F
ArticleID:ANIE201203768
Deutsche Forschungsgemeinschaft
Support from the Freiburg Institute for Advanced Studies (FRIAS), the Deutsche Forschungsgemeinschaft (IRTG 1038), and the Fonds der chemischen Industrie (PhD fellowship to U.G.) is gratefully acknowledged. We thank S. Diezel for support with the kinetic experiments, J. Schäfer for help with X-ray structure analysis, and Dr. M. Cooke and Prof. Dr. D. Plattner for stimulating discussions.
Freiburg Institute for Advanced Studies (FRIAS)
Fonds der chemischen Industrie
Support from the Freiburg Institute for Advanced Studies (FRIAS), the Deutsche Forschungsgemeinschaft (IRTG 1038), and the Fonds der chemischen Industrie (PhD fellowship to U.G.) is gratefully acknowledged. We thank S. Diezel for support with the kinetic experiments, J. Schäfer for help with X‐ray structure analysis, and Dr. M. Cooke and Prof. Dr. D. Plattner for stimulating discussions.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201203768