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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...

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Autores principales: Zirakzadeh, Afrooz, Groß, Manuela A., Wang, Yaping, Mereiter, Kurt, Spindler, Felix, Weissensteiner, Walter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2013
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.
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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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