Taming a Functional Group: Creating Air-Stable, Chiral Primary Phosphanes

No rings of fire! Enantiopure primary phosphanes have been developed which are remarkably stable to air oxidation in both solid and solution states (see example). This new class of stable ligand synthon appears to owe its stability to conjugation in their aryl backbones with the extended π ring syst...

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Published inAngewandte Chemie International Edition Vol. 45; no. 43; pp. 7248 - 7251
Main Authors Hiney, Rachel M., Higham, Lee J., Müller-Bunz, Helge, Gilheany, Declan G.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 06.11.2006
WILEY‐VCH Verlag
Wiley
Subjects
Air
air stability
asymmetric catalysis
Chemistry
Chemistry, Multidisciplinary
conjugation
Crystallography, X-Ray
electrochemistry
Models, Molecular
Molecular Structure
Oxidation-Reduction
phosphanes
Phosphines - chemical synthesis
Phosphines - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
DESIGN
ASYMMETRIC-SYNTHESIS
HYDROGENATION
OXIDE
electrochemistry
CRYSTAL
asymmetric catalysis
air stability
phosphanes
PRIMARY PHOSPHINES
conjugation
LIGANDS
CHEMISTRY
BOND
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Summary:No rings of fire! Enantiopure primary phosphanes have been developed which are remarkably stable to air oxidation in both solid and solution states (see example). This new class of stable ligand synthon appears to owe its stability to conjugation in their aryl backbones with the extended π ring system. Even one extra ring is good enough.
Bibliography:Irish Research Council for Science, Engineering, and Technology (IRCSET)
ark:/67375/WNG-8P471296-8
EU - No. HMPD-CT-2000-00053
ArticleID:ANIE200602143
We thank the Irish Research Council for Science, Engineering, and Technology (IRCSET) for a scholarship for R.M.H. and the EU for a Marie Curie Host Development Fellowship (HMPD-CT-2000-00053) for L.J.H. We also thank Prof. R. O'Neill for electrochemistry advice and apparatus as well as Dr. G. Docherty (Rhodia) for discussions on phenylphosphane.
istex:62194D1A3E0F0723FC6FF37D7988C4262EE29759
We thank the Irish Research Council for Science, Engineering, and Technology (IRCSET) for a scholarship for R.M.H. and the EU for a Marie Curie Host Development Fellowship (HMPD‐CT‐2000‐00053) for L.J.H. We also thank Prof. R. O'Neill for electrochemistry advice and apparatus as well as Dr. G. Docherty (Rhodia) for discussions on phenylphosphane.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200602143