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
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Abstract 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.
AbstractList 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.
Author Gilheany, Declan G.
Higham, Lee J.
Hiney, Rachel M.
Müller-Bunz, Helge
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  surname: Hiney
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  organization: School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical Biology, Conway Institute for Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland, Fax: (+353) 1-716-2127
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  givenname: Lee J.
  surname: Higham
  fullname: Higham, Lee J.
  email: lee.higham@ucd.ie
  organization: School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical Biology, Conway Institute for Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland, Fax: (+353) 1-716-2127
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  givenname: Helge
  surname: Müller-Bunz
  fullname: Müller-Bunz, Helge
  organization: School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical Biology, Conway Institute for Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland, Fax: (+353) 1-716-2127
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  givenname: Declan G.
  surname: Gilheany
  fullname: Gilheany, Declan G.
  email: declan.gilheany@ucd.ie
  organization: School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical Biology, Conway Institute for Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland, Fax: (+353) 1-716-2127
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Issue 43
Keywords DESIGN
ASYMMETRIC-SYNTHESIS
HYDROGENATION
OXIDE
electrochemistry
CRYSTAL
asymmetric catalysis
air stability
phosphanes
PRIMARY PHOSPHINES
conjugation
LIGANDS
CHEMISTRY
BOND
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Notes Irish Research Council for Science, Engineering, and Technology (IRCSET)
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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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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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e_1_2_2_4_2
e_1_2_2_22_2
e_1_2_2_49_2
e_1_2_2_6_2
e_1_2_2_20_2
e_1_2_2_41_2
e_1_2_2_8_2
e_1_2_2_28_2
e_1_2_2_43_2
e_1_2_2_26_2
e_1_2_2_45_2
e_1_2_2_13_2
e_1_2_2_36_2
e_1_2_2_11_2
e_1_2_2_38_2
e_1_2_2_51_2
e_1_2_2_19_2
e_1_2_2_30_2
e_1_2_2_53_2
e_1_2_2_17_2
e_1_2_2_32_2
e_1_2_2_15_2
e_1_2_2_34_2
e_1_2_2_3_2
e_1_2_2_23_2
e_1_2_2_48_2
e_1_2_2_5_2
e_1_2_2_21_2
e_1_2_2_1_2
e_1_2_2_29_2
e_1_2_2_42_2
e_1_2_2_7_2
e_1_2_2_27_2
e_1_2_2_44_2
e_1_2_2_25_3
e_1_2_2_9_2
e_1_2_2_25_2
e_1_2_2_46_2
Hudson H. R. (e_1_2_2_40_2) 1990
e_1_2_2_12_3
e_1_2_2_12_2
e_1_2_2_37_2
e_1_2_2_10_2
e_1_2_2_39_2
e_1_2_2_50_2
e_1_2_2_18_2
e_1_2_2_31_2
e_1_2_2_52_2
e_1_2_2_16_2
e_1_2_2_33_2
e_1_2_2_33_3
e_1_2_2_14_2
e_1_2_2_33_4
e_1_2_2_35_2
Maier L. (e_1_2_2_2_2) 1972
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Snippet No rings of fire! Enantiopure primary phosphanes have been developed which are remarkably stable to air oxidation in both solid and solution states (see...
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SubjectTerms 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
Title Taming a Functional Group: Creating Air-Stable, Chiral Primary Phosphanes
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https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.200602143
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Volume 45
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