---
_id: '64005'
abstract:
- lang: eng
  text: A novel immobilized chiral dirhodium catalyst, Rh2(S-PTTL)3(S-PTTL-linker)∼SBA-15
    (8), has been prepared via click reaction of azide-groups on functionalized SBA-15
    with the dirhodium complex Rh2(S-PTTL)3(S-PTTL-alkyne) (6) containing an alkyne
    moiety. During the synthesis of this complex, one chiral ligand of the parent
    Rh2(S-PTTL)4 catalyst is exchanged with an analogous chiral ligand system containing
    an alkyne moiety, which to a great extent maintains the intrinsic catalytic performance
    of the catalyst. The heterogeneous dirhodium catalyst is characterized by FT-IR
    and 13C solid-state NMR to validate the successful immobilization. The catalytic
    performance of the heterogeneous catalyst 8 is investigated in the asymmetric
    cyclopropanation of 3-diazooxindole with different aryl alkenes that form spiro-cyclopropyloxindoles
    which serve as precursors for pharmaceuticals. The resulting heterogeneous catalyst
    shows high catalytic activity and significant enantioselectivity. Importantly,
    it can be readily recovered and reused at least four times without significant
    loss of its catalytic performance.
author:
- first_name: Zhenzhong
  full_name: Li, Zhenzhong
  last_name: Li
- first_name: Lorenz
  full_name: Rösler, Lorenz
  last_name: Rösler
- first_name: Till
  full_name: Wissel, Till
  last_name: Wissel
- first_name: Hergen
  full_name: Breitzke, Hergen
  last_name: Breitzke
- first_name: Torsten
  full_name: Gutmann, Torsten
  id: '118165'
  last_name: Gutmann
- first_name: Gerd
  full_name: Buntkowsky, Gerd
  last_name: Buntkowsky
citation:
  ama: 'Li Z, Rösler L, Wissel T, Breitzke H, Gutmann T, Buntkowsky G. Immobilization
    of a chiral dirhodium catalyst on SBA-15 via click-chemistry: Application in the
    asymmetric cyclopropanation of 3-diazooxindole with aryl alkenes. <i>Journal of
    CO2 Utilization</i>. 2021;52:101682. doi:<a href="https://doi.org/10.1016/j.jcou.2021.101682">10.1016/j.jcou.2021.101682</a>'
  apa: 'Li, Z., Rösler, L., Wissel, T., Breitzke, H., Gutmann, T., &#38; Buntkowsky,
    G. (2021). Immobilization of a chiral dirhodium catalyst on SBA-15 via click-chemistry:
    Application in the asymmetric cyclopropanation of 3-diazooxindole with aryl alkenes.
    <i>Journal of CO2 Utilization</i>, <i>52</i>, 101682. <a href="https://doi.org/10.1016/j.jcou.2021.101682">https://doi.org/10.1016/j.jcou.2021.101682</a>'
  bibtex: '@article{Li_Rösler_Wissel_Breitzke_Gutmann_Buntkowsky_2021, title={Immobilization
    of a chiral dirhodium catalyst on SBA-15 via click-chemistry: Application in the
    asymmetric cyclopropanation of 3-diazooxindole with aryl alkenes}, volume={52},
    DOI={<a href="https://doi.org/10.1016/j.jcou.2021.101682">10.1016/j.jcou.2021.101682</a>},
    journal={Journal of CO2 Utilization}, author={Li, Zhenzhong and Rösler, Lorenz
    and Wissel, Till and Breitzke, Hergen and Gutmann, Torsten and Buntkowsky, Gerd},
    year={2021}, pages={101682} }'
  chicago: 'Li, Zhenzhong, Lorenz Rösler, Till Wissel, Hergen Breitzke, Torsten Gutmann,
    and Gerd Buntkowsky. “Immobilization of a Chiral Dirhodium Catalyst on SBA-15
    via Click-Chemistry: Application in the Asymmetric Cyclopropanation of 3-Diazooxindole
    with Aryl Alkenes.” <i>Journal of CO2 Utilization</i> 52 (2021): 101682. <a href="https://doi.org/10.1016/j.jcou.2021.101682">https://doi.org/10.1016/j.jcou.2021.101682</a>.'
  ieee: 'Z. Li, L. Rösler, T. Wissel, H. Breitzke, T. Gutmann, and G. Buntkowsky,
    “Immobilization of a chiral dirhodium catalyst on SBA-15 via click-chemistry:
    Application in the asymmetric cyclopropanation of 3-diazooxindole with aryl alkenes,”
    <i>Journal of CO2 Utilization</i>, vol. 52, p. 101682, 2021, doi: <a href="https://doi.org/10.1016/j.jcou.2021.101682">10.1016/j.jcou.2021.101682</a>.'
  mla: 'Li, Zhenzhong, et al. “Immobilization of a Chiral Dirhodium Catalyst on SBA-15
    via Click-Chemistry: Application in the Asymmetric Cyclopropanation of 3-Diazooxindole
    with Aryl Alkenes.” <i>Journal of CO2 Utilization</i>, vol. 52, 2021, p. 101682,
    doi:<a href="https://doi.org/10.1016/j.jcou.2021.101682">10.1016/j.jcou.2021.101682</a>.'
  short: Z. Li, L. Rösler, T. Wissel, H. Breitzke, T. Gutmann, G. Buntkowsky, Journal
    of CO2 Utilization 52 (2021) 101682.
date_created: 2026-02-07T15:55:18Z
date_updated: 2026-02-17T16:15:35Z
doi: 10.1016/j.jcou.2021.101682
extern: '1'
intvolume: '        52'
keyword:
- immobilized catalyst
- asymmetric cyclopropanation
- Chiral dirhodium
language:
- iso: eng
page: '101682'
publication: Journal of CO2 Utilization
status: public
title: 'Immobilization of a chiral dirhodium catalyst on SBA-15 via click-chemistry:
  Application in the asymmetric cyclopropanation of 3-diazooxindole with aryl alkenes'
type: journal_article
user_id: '100715'
volume: 52
year: '2021'
...
---
_id: '63956'
abstract:
- lang: eng
  text: The synthesis of novel robust and stable iridium-based immobilized catalysts
    on silica-polymer hybrid materials (Si-PB-Ir) is described. These catalysts are
    characterized by a combination of 1D P-31 CP-MAS and 2D P-31-H-1 HETCOR and J-resolved
    multinuclear solid state NMR experiments. Different binding situations such as
    singly and multiply coordinated phosphines are identified. Density functional
    theory (DFT) calculations are performed to corroborate the interpretation of the
    experimental NMR data, in order to propose a structural model of the heterogenized
    catalysts. Finally, the catalytic activity of the Si-PB-Ir catalysts is investigated
    for the hydrogenation of styrene employing para-enriched hydrogen gas.
author:
- first_name: Torsten
  full_name: Gutmann, Torsten
  id: '118165'
  last_name: Gutmann
- first_name: S.
  full_name: Alkhagani, S.
  last_name: Alkhagani
- first_name: N.
  full_name: Rothermel, N.
  last_name: Rothermel
- first_name: H. H.
  full_name: Limbach, H. H.
  last_name: Limbach
- first_name: H.
  full_name: Breitzke, H.
  last_name: Breitzke
- first_name: G.
  full_name: Buntkowsky, G.
  last_name: Buntkowsky
citation:
  ama: Gutmann T, Alkhagani S, Rothermel N, Limbach HH, Breitzke H, Buntkowsky G.
    P-31-Solid-State NMR Characterization and Catalytic Hydrogenation Tests of Novel
    heterogenized Iridium-Catalysts. <i>Zeitschrift Fur Physikalische Chemie-International
    Journal of Research in Physical Chemistry &#38; Chemical Physics</i>. 2017;231(3):653–669.
    doi:<a href="https://doi.org/10.1515/zpch-2016-0837">10.1515/zpch-2016-0837</a>
  apa: Gutmann, T., Alkhagani, S., Rothermel, N., Limbach, H. H., Breitzke, H., &#38;
    Buntkowsky, G. (2017). P-31-Solid-State NMR Characterization and Catalytic Hydrogenation
    Tests of Novel heterogenized Iridium-Catalysts. <i>Zeitschrift Fur Physikalische
    Chemie-International Journal of Research in Physical Chemistry &#38; Chemical
    Physics</i>, <i>231</i>(3), 653–669. <a href="https://doi.org/10.1515/zpch-2016-0837">https://doi.org/10.1515/zpch-2016-0837</a>
  bibtex: '@article{Gutmann_Alkhagani_Rothermel_Limbach_Breitzke_Buntkowsky_2017,
    title={P-31-Solid-State NMR Characterization and Catalytic Hydrogenation Tests
    of Novel heterogenized Iridium-Catalysts}, volume={231}, DOI={<a href="https://doi.org/10.1515/zpch-2016-0837">10.1515/zpch-2016-0837</a>},
    number={3}, journal={Zeitschrift Fur Physikalische Chemie-International Journal
    of Research in Physical Chemistry &#38; Chemical Physics}, author={Gutmann, Torsten
    and Alkhagani, S. and Rothermel, N. and Limbach, H. H. and Breitzke, H. and Buntkowsky,
    G.}, year={2017}, pages={653–669} }'
  chicago: 'Gutmann, Torsten, S. Alkhagani, N. Rothermel, H. H. Limbach, H. Breitzke,
    and G. Buntkowsky. “P-31-Solid-State NMR Characterization and Catalytic Hydrogenation
    Tests of Novel Heterogenized Iridium-Catalysts.” <i>Zeitschrift Fur Physikalische
    Chemie-International Journal of Research in Physical Chemistry &#38; Chemical
    Physics</i> 231, no. 3 (2017): 653–669. <a href="https://doi.org/10.1515/zpch-2016-0837">https://doi.org/10.1515/zpch-2016-0837</a>.'
  ieee: 'T. Gutmann, S. Alkhagani, N. Rothermel, H. H. Limbach, H. Breitzke, and G.
    Buntkowsky, “P-31-Solid-State NMR Characterization and Catalytic Hydrogenation
    Tests of Novel heterogenized Iridium-Catalysts,” <i>Zeitschrift Fur Physikalische
    Chemie-International Journal of Research in Physical Chemistry &#38; Chemical
    Physics</i>, vol. 231, no. 3, pp. 653–669, 2017, doi: <a href="https://doi.org/10.1515/zpch-2016-0837">10.1515/zpch-2016-0837</a>.'
  mla: Gutmann, Torsten, et al. “P-31-Solid-State NMR Characterization and Catalytic
    Hydrogenation Tests of Novel Heterogenized Iridium-Catalysts.” <i>Zeitschrift
    Fur Physikalische Chemie-International Journal of Research in Physical Chemistry
    &#38; Chemical Physics</i>, vol. 231, no. 3, 2017, pp. 653–669, doi:<a href="https://doi.org/10.1515/zpch-2016-0837">10.1515/zpch-2016-0837</a>.
  short: T. Gutmann, S. Alkhagani, N. Rothermel, H.H. Limbach, H. Breitzke, G. Buntkowsky,
    Zeitschrift Fur Physikalische Chemie-International Journal of Research in Physical
    Chemistry &#38; Chemical Physics 231 (2017) 653–669.
date_created: 2026-02-07T15:35:41Z
date_updated: 2026-02-17T16:18:04Z
doi: 10.1515/zpch-2016-0837
extern: '1'
intvolume: '       231'
issue: '3'
keyword:
- Chemistry
- dynamic nuclear-polarization
- solid-state nmr
- DFT
- heterogeneous catalysis
- hydrido complexes
- hydrogenation
- immobilized catalyst
- inorganic hybrid
- iridium
- materials
- mesoporous
- molecular-orbital methods
- PHIP
- phosphine complexes
- reusable catalysts
- silica
- solid-state-NMR
- wilkinsons catalyst
language:
- iso: eng
page: 653–669
publication: Zeitschrift Fur Physikalische Chemie-International Journal of Research
  in Physical Chemistry & Chemical Physics
publication_identifier:
  issn:
  - 0942-9352
status: public
title: P-31-Solid-State NMR Characterization and Catalytic Hydrogenation Tests of
  Novel heterogenized Iridium-Catalysts
type: journal_article
user_id: '100715'
volume: 231
year: '2017'
...
---
_id: '63963'
abstract:
- lang: eng
  text: A novel heterogeneous dirhodium catalyst has been synthesized. This stable
    catalyst is constructed from dirhodium acetate dimer (Rh2(OAc)4) units, which
    are covalently linked to amine- and carboxyl-bifunctionalized mesoporous silica
    (SBA-15NH2COOH). It shows good efficiency in catalyzing the cyclopropanation
    reaction of styrene and ethyl diazoacetate (EDA) forming cis- and trans-1-ethoxycarbonyl-2-phenylcyclopropane.
    To characterize the structure of this catalyst and to confirm the successful immobilization,
    heteronuclear solid-state NMR experiments have been performed. The high application
    potential of dynamic nuclear polarization (DNP) NMR for the analysis of binding
    sites in this novel catalyst is demonstrated. Signal-enhanced 13C CP MAS and 15N
    CP MAS techniques have been employed to detect different carboxyl and amine binding
    sites in natural abundance on a fast time scale. The interpretation of the experimental
    chemical shift values for different binding sites has been corroborated by quantum
    chemical calculations on dirhodium model complexes.
author:
- first_name: Torsten
  full_name: Gutmann, Torsten
  id: '118165'
  last_name: Gutmann
- first_name: Jiquan
  full_name: Liu, Jiquan
  last_name: Liu
- first_name: Niels
  full_name: Rothermel, Niels
  last_name: Rothermel
- first_name: Yeping
  full_name: Xu, Yeping
  last_name: Xu
- first_name: Eva
  full_name: Jaumann, Eva
  last_name: Jaumann
- first_name: Mayke
  full_name: Werner, Mayke
  last_name: Werner
- first_name: Hergen
  full_name: Breitzke, Hergen
  last_name: Breitzke
- first_name: Snorri T.
  full_name: Sigurdsson, Snorri T.
  last_name: Sigurdsson
- first_name: Gerd
  full_name: Buntkowsky, Gerd
  last_name: Buntkowsky
citation:
  ama: 'Gutmann T, Liu J, Rothermel N, et al. Natural Abundance 15N NMR by Dynamic
    Nuclear Polarization: Fast Analysis of Binding Sites of a Novel Amine-Carboxyl-Linked
    Immobilized Dirhodium Catalyst. <i>Chemistry A European Journal</i>. 2015;21(9):3798–3805.
    doi:<a href="https://doi.org/10.1002/chem.201405043">10.1002/chem.201405043</a>'
  apa: 'Gutmann, T., Liu, J., Rothermel, N., Xu, Y., Jaumann, E., Werner, M., Breitzke,
    H., Sigurdsson, S. T., &#38; Buntkowsky, G. (2015). Natural Abundance 15N NMR
    by Dynamic Nuclear Polarization: Fast Analysis of Binding Sites of a Novel Amine-Carboxyl-Linked
    Immobilized Dirhodium Catalyst. <i>Chemistry A European Journal</i>, <i>21</i>(9),
    3798–3805. <a href="https://doi.org/10.1002/chem.201405043">https://doi.org/10.1002/chem.201405043</a>'
  bibtex: '@article{Gutmann_Liu_Rothermel_Xu_Jaumann_Werner_Breitzke_Sigurdsson_Buntkowsky_2015,
    title={Natural Abundance 15N NMR by Dynamic Nuclear Polarization: Fast Analysis
    of Binding Sites of a Novel Amine-Carboxyl-Linked Immobilized Dirhodium Catalyst},
    volume={21}, DOI={<a href="https://doi.org/10.1002/chem.201405043">10.1002/chem.201405043</a>},
    number={9}, journal={Chemistry A European Journal}, publisher={WILEY-VCH Verlag},
    author={Gutmann, Torsten and Liu, Jiquan and Rothermel, Niels and Xu, Yeping and
    Jaumann, Eva and Werner, Mayke and Breitzke, Hergen and Sigurdsson, Snorri T.
    and Buntkowsky, Gerd}, year={2015}, pages={3798–3805} }'
  chicago: 'Gutmann, Torsten, Jiquan Liu, Niels Rothermel, Yeping Xu, Eva Jaumann,
    Mayke Werner, Hergen Breitzke, Snorri T. Sigurdsson, and Gerd Buntkowsky. “Natural
    Abundance 15N NMR by Dynamic Nuclear Polarization: Fast Analysis of Binding Sites
    of a Novel Amine-Carboxyl-Linked Immobilized Dirhodium Catalyst.” <i>Chemistry
    A European Journal</i> 21, no. 9 (2015): 3798–3805. <a href="https://doi.org/10.1002/chem.201405043">https://doi.org/10.1002/chem.201405043</a>.'
  ieee: 'T. Gutmann <i>et al.</i>, “Natural Abundance 15N NMR by Dynamic Nuclear Polarization:
    Fast Analysis of Binding Sites of a Novel Amine-Carboxyl-Linked Immobilized Dirhodium
    Catalyst,” <i>Chemistry A European Journal</i>, vol. 21, no. 9, pp. 3798–3805,
    2015, doi: <a href="https://doi.org/10.1002/chem.201405043">10.1002/chem.201405043</a>.'
  mla: 'Gutmann, Torsten, et al. “Natural Abundance 15N NMR by Dynamic Nuclear Polarization:
    Fast Analysis of Binding Sites of a Novel Amine-Carboxyl-Linked Immobilized Dirhodium
    Catalyst.” <i>Chemistry A European Journal</i>, vol. 21, no. 9, WILEY-VCH Verlag,
    2015, pp. 3798–3805, doi:<a href="https://doi.org/10.1002/chem.201405043">10.1002/chem.201405043</a>.'
  short: T. Gutmann, J. Liu, N. Rothermel, Y. Xu, E. Jaumann, M. Werner, H. Breitzke,
    S.T. Sigurdsson, G. Buntkowsky, Chemistry A European Journal 21 (2015) 3798–3805.
date_created: 2026-02-07T15:38:07Z
date_updated: 2026-02-17T16:17:50Z
doi: 10.1002/chem.201405043
extern: '1'
intvolume: '        21'
issue: '9'
keyword:
- heterogeneous catalysis
- immobilized catalyst
- dynamic nuclear polarization
- hyperpolarization
- NMR spectroscopy
language:
- iso: eng
page: 3798–3805
publication: Chemistry A European Journal
publisher: WILEY-VCH Verlag
status: public
title: 'Natural Abundance 15N NMR by Dynamic Nuclear Polarization: Fast Analysis of
  Binding Sites of a Novel Amine-Carboxyl-Linked Immobilized Dirhodium Catalyst'
type: journal_article
user_id: '100715'
volume: 21
year: '2015'
...