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Biferrocene-Based Diphosphine Ligands: Synthesis and Application of Walphos Analogues in Asymmetric Hydrogenations
[Image: see text] A total of four biferrocene-based Walphos-type ligands have been synthesized, structurally characterized, and tested in the rhodium-, ruthenium- and iridium-catalyzed hydrogenation of alkenes and ketones. Negishi coupling conditions allowed the biferrocene backbone of these diphosp...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2013
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3584622/ https://www.ncbi.nlm.nih.gov/pubmed/23457421 http://dx.doi.org/10.1021/om3012147 |
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author | Zirakzadeh, Afrooz Groß, Manuela A. Wang, Yaping Mereiter, Kurt Spindler, Felix Weissensteiner, Walter |
author_facet | Zirakzadeh, Afrooz Groß, Manuela A. Wang, Yaping Mereiter, Kurt Spindler, Felix Weissensteiner, Walter |
author_sort | Zirakzadeh, Afrooz |
collection | PubMed |
description | [Image: see text] A total of four biferrocene-based Walphos-type ligands have been synthesized, structurally characterized, and tested in the rhodium-, ruthenium- and iridium-catalyzed hydrogenation of alkenes and ketones. Negishi coupling conditions allowed the biferrocene backbone of these diphosphine ligands to be built up diastereoselectively from the two nonidentical and nonracemic ferrocene fragments (R)-1-(N,N-dimethylamino)ethylferrocene and (S(Fc))-2-bromoiodoferrocene. The molecular structures of (S(Fc))-2-bromoiodoferrocene, the coupling product, two ligands, and the two complexes ([PdCl(2)(L)] and [RuCl(p-cymene)(L)]PF(6)) were determined by X-ray diffraction. The structural features of complexes and the catalysis results obtained with the newly synthesized biferrocene-based ligands were compared with those of the corresponding Walphos ligands. |
format | Online Article Text |
id | pubmed-3584622 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-35846222013-02-28 Biferrocene-Based Diphosphine Ligands: Synthesis and Application of Walphos Analogues in Asymmetric Hydrogenations Zirakzadeh, Afrooz Groß, Manuela A. Wang, Yaping Mereiter, Kurt Spindler, Felix Weissensteiner, Walter Organometallics [Image: see text] A total of four biferrocene-based Walphos-type ligands have been synthesized, structurally characterized, and tested in the rhodium-, ruthenium- and iridium-catalyzed hydrogenation of alkenes and ketones. Negishi coupling conditions allowed the biferrocene backbone of these diphosphine ligands to be built up diastereoselectively from the two nonidentical and nonracemic ferrocene fragments (R)-1-(N,N-dimethylamino)ethylferrocene and (S(Fc))-2-bromoiodoferrocene. The molecular structures of (S(Fc))-2-bromoiodoferrocene, the coupling product, two ligands, and the two complexes ([PdCl(2)(L)] and [RuCl(p-cymene)(L)]PF(6)) were determined by X-ray diffraction. The structural features of complexes and the catalysis results obtained with the newly synthesized biferrocene-based ligands were compared with those of the corresponding Walphos ligands. American Chemical Society 2013-02-11 2013-02-25 /pmc/articles/PMC3584622/ /pubmed/23457421 http://dx.doi.org/10.1021/om3012147 Text en Copyright © 2013 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) |
spellingShingle | Zirakzadeh, Afrooz Groß, Manuela A. Wang, Yaping Mereiter, Kurt Spindler, Felix Weissensteiner, Walter Biferrocene-Based Diphosphine Ligands: Synthesis and Application of Walphos Analogues in Asymmetric Hydrogenations |
title | Biferrocene-Based Diphosphine
Ligands: Synthesis and
Application of Walphos Analogues in Asymmetric Hydrogenations |
title_full | Biferrocene-Based Diphosphine
Ligands: Synthesis and
Application of Walphos Analogues in Asymmetric Hydrogenations |
title_fullStr | Biferrocene-Based Diphosphine
Ligands: Synthesis and
Application of Walphos Analogues in Asymmetric Hydrogenations |
title_full_unstemmed | Biferrocene-Based Diphosphine
Ligands: Synthesis and
Application of Walphos Analogues in Asymmetric Hydrogenations |
title_short | Biferrocene-Based Diphosphine
Ligands: Synthesis and
Application of Walphos Analogues in Asymmetric Hydrogenations |
title_sort | biferrocene-based diphosphine
ligands: synthesis and
application of walphos analogues in asymmetric hydrogenations |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3584622/ https://www.ncbi.nlm.nih.gov/pubmed/23457421 http://dx.doi.org/10.1021/om3012147 |
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