---
_id: '35686'
abstract:
- lang: eng
  text: <jats:title>Abstract</jats:title><jats:p>The development of the frustrated
    Lewis pair catalyzed hydrogenation of tertiary and secondary amides is reviewed.
    Detailed insight into our strategies in order to overcome challenges during the
    reaction development process is provided. Furthermore, the developed chemistry
    is extended to the hydrogenation of polyamides and of trifluoroacetamides for
    the convenient introduction of trifluoroethyl groups into organic molecules.</jats:p>
author:
- first_name: Jan
  full_name: Paradies, Jan
  id: '53339'
  last_name: Paradies
  orcid: 0000-0002-3698-668X
- first_name: Laura
  full_name: Köring, Laura
  last_name: Köring
- first_name: Nikolai A.
  full_name: Sitte, Nikolai A.
  last_name: Sitte
citation:
  ama: Paradies J, Köring L, Sitte NA. Towards the Development of Frustrated Lewis
    Pair (FLP) Catalyzed Hydrogenations of Tertiary and Secondary Carboxylic Amides.
    <i>Synthesis</i>. 2021;54(05):1287-1300. doi:<a href="https://doi.org/10.1055/a-1681-3972">10.1055/a-1681-3972</a>
  apa: Paradies, J., Köring, L., &#38; Sitte, N. A. (2021). Towards the Development
    of Frustrated Lewis Pair (FLP) Catalyzed Hydrogenations of Tertiary and Secondary
    Carboxylic Amides. <i>Synthesis</i>, <i>54</i>(05), 1287–1300. <a href="https://doi.org/10.1055/a-1681-3972">https://doi.org/10.1055/a-1681-3972</a>
  bibtex: '@article{Paradies_Köring_Sitte_2021, title={Towards the Development of
    Frustrated Lewis Pair (FLP) Catalyzed Hydrogenations of Tertiary and Secondary
    Carboxylic Amides}, volume={54}, DOI={<a href="https://doi.org/10.1055/a-1681-3972">10.1055/a-1681-3972</a>},
    number={05}, journal={Synthesis}, publisher={Georg Thieme Verlag KG}, author={Paradies,
    Jan and Köring, Laura and Sitte, Nikolai A.}, year={2021}, pages={1287–1300} }'
  chicago: 'Paradies, Jan, Laura Köring, and Nikolai A. Sitte. “Towards the Development
    of Frustrated Lewis Pair (FLP) Catalyzed Hydrogenations of Tertiary and Secondary
    Carboxylic Amides.” <i>Synthesis</i> 54, no. 05 (2021): 1287–1300. <a href="https://doi.org/10.1055/a-1681-3972">https://doi.org/10.1055/a-1681-3972</a>.'
  ieee: 'J. Paradies, L. Köring, and N. A. Sitte, “Towards the Development of Frustrated
    Lewis Pair (FLP) Catalyzed Hydrogenations of Tertiary and Secondary Carboxylic
    Amides,” <i>Synthesis</i>, vol. 54, no. 05, pp. 1287–1300, 2021, doi: <a href="https://doi.org/10.1055/a-1681-3972">10.1055/a-1681-3972</a>.'
  mla: Paradies, Jan, et al. “Towards the Development of Frustrated Lewis Pair (FLP)
    Catalyzed Hydrogenations of Tertiary and Secondary Carboxylic Amides.” <i>Synthesis</i>,
    vol. 54, no. 05, Georg Thieme Verlag KG, 2021, pp. 1287–300, doi:<a href="https://doi.org/10.1055/a-1681-3972">10.1055/a-1681-3972</a>.
  short: J. Paradies, L. Köring, N.A. Sitte, Synthesis 54 (2021) 1287–1300.
date_created: 2023-01-10T08:56:44Z
date_updated: 2023-01-23T12:51:23Z
doi: 10.1055/a-1681-3972
intvolume: '        54'
issue: '05'
keyword:
- Organic Chemistry
- Catalysis
language:
- iso: eng
page: 1287-1300
publication: Synthesis
publication_identifier:
  issn:
  - 0039-7881
  - 1437-210X
publication_status: published
publisher: Georg Thieme Verlag KG
status: public
title: Towards the Development of Frustrated Lewis Pair (FLP) Catalyzed Hydrogenations
  of Tertiary and Secondary Carboxylic Amides
type: journal_article
user_id: '53339'
volume: 54
year: '2021'
...
---
_id: '37946'
abstract:
- lang: eng
  text: <jats:title>Abstract</jats:title><jats:p>The facile synthesis of highly functionalized
    building blocks with potential biological activity is of great interest to medicinal
    chemistry. The benzoxepinone core structures commonly exhibit biological activity.
    Thus, a short and efficient synthetic route towards benzoxepine containing scaffold,
    which enables late stage modification was developed. Namely, base-free catalytic
    Wittig reactions enabled the synthesis of bromobenzoxepinones from readily available
    starting materials. Subsequent, Suzuki–Miyaura and Stille reactions proved to
    be suitable methods to access a variety of benzoxepinone diaryl derivatives by
    late stage modification in only three steps. This three-step reaction sequence
    is suitable for high throughput applications and gives facile access to highly
    complex molecular structures, which are suitable for further functionalization.
    The antiproliferative properties of selected arylbenzoxepinones­ were tested in
    vitro on monolayer tumor cell line A549. Notably, in this initial screening, these
    compounds were found to be active in the micromolar range.</jats:p>
author:
- first_name: Thomas
  full_name: Werner, Thomas
  id: '89271'
  last_name: Werner
  orcid: 0000-0001-9025-3244
- first_name: Aiga
  full_name: Grandane, Aiga
  last_name: Grandane
- first_name: Linda
  full_name: Pudnika, Linda
  last_name: Pudnika
- first_name: Ilona
  full_name: Domraceva, Ilona
  last_name: Domraceva
- first_name: Raivis
  full_name: Zalubovskis, Raivis
  last_name: Zalubovskis
citation:
  ama: Werner T, Grandane A, Pudnika L, Domraceva I, Zalubovskis R. Base-Free Catalytic
    Wittig-/Cross-Coupling Reaction Sequence as Short Synthetic Strategy for the Preparation of
    Highly Functionalized Arylbenzoxepinones. <i>Synthesis</i>. 2021;53(19):3545-3554.
    doi:<a href="https://doi.org/10.1055/a-1509-6078">10.1055/a-1509-6078</a>
  apa: Werner, T., Grandane, A., Pudnika, L., Domraceva, I., &#38; Zalubovskis, R.
    (2021). Base-Free Catalytic Wittig-/Cross-Coupling Reaction Sequence as Short
    Synthetic Strategy for the Preparation of Highly Functionalized Arylbenzoxepinones.
    <i>Synthesis</i>, <i>53</i>(19), 3545–3554. <a href="https://doi.org/10.1055/a-1509-6078">https://doi.org/10.1055/a-1509-6078</a>
  bibtex: '@article{Werner_Grandane_Pudnika_Domraceva_Zalubovskis_2021, title={Base-Free
    Catalytic Wittig-/Cross-Coupling Reaction Sequence as Short Synthetic Strategy
    for the Preparation of Highly Functionalized Arylbenzoxepinones}, volume={53},
    DOI={<a href="https://doi.org/10.1055/a-1509-6078">10.1055/a-1509-6078</a>}, number={19},
    journal={Synthesis}, publisher={Georg Thieme Verlag KG}, author={Werner, Thomas
    and Grandane, Aiga and Pudnika, Linda and Domraceva, Ilona and Zalubovskis, Raivis},
    year={2021}, pages={3545–3554} }'
  chicago: 'Werner, Thomas, Aiga Grandane, Linda Pudnika, Ilona Domraceva, and Raivis
    Zalubovskis. “Base-Free Catalytic Wittig-/Cross-Coupling Reaction Sequence as
    Short Synthetic Strategy for the Preparation of Highly Functionalized Arylbenzoxepinones.”
    <i>Synthesis</i> 53, no. 19 (2021): 3545–54. <a href="https://doi.org/10.1055/a-1509-6078">https://doi.org/10.1055/a-1509-6078</a>.'
  ieee: 'T. Werner, A. Grandane, L. Pudnika, I. Domraceva, and R. Zalubovskis, “Base-Free
    Catalytic Wittig-/Cross-Coupling Reaction Sequence as Short Synthetic Strategy
    for the Preparation of Highly Functionalized Arylbenzoxepinones,” <i>Synthesis</i>,
    vol. 53, no. 19, pp. 3545–3554, 2021, doi: <a href="https://doi.org/10.1055/a-1509-6078">10.1055/a-1509-6078</a>.'
  mla: Werner, Thomas, et al. “Base-Free Catalytic Wittig-/Cross-Coupling Reaction
    Sequence as Short Synthetic Strategy for the Preparation of Highly Functionalized
    Arylbenzoxepinones.” <i>Synthesis</i>, vol. 53, no. 19, Georg Thieme Verlag KG,
    2021, pp. 3545–54, doi:<a href="https://doi.org/10.1055/a-1509-6078">10.1055/a-1509-6078</a>.
  short: T. Werner, A. Grandane, L. Pudnika, I. Domraceva, R. Zalubovskis, Synthesis
    53 (2021) 3545–3554.
date_created: 2023-01-22T20:27:34Z
date_updated: 2025-11-10T08:47:47Z
department:
- _id: '35'
- _id: '2'
- _id: '657'
doi: 10.1055/a-1509-6078
intvolume: '        53'
issue: '19'
keyword:
- T2
- T4
- CSSD
language:
- iso: eng
page: 3545-3554
publication: Synthesis
publication_identifier:
  issn:
  - 0039-7881
  - 1437-210X
publication_status: published
publisher: Georg Thieme Verlag KG
status: public
title: Base-Free Catalytic Wittig-/Cross-Coupling Reaction Sequence as Short Synthetic
  Strategy for the Preparation of Highly Functionalized Arylbenzoxepinones
type: journal_article
user_id: '89271'
volume: 53
year: '2021'
...
---
_id: '38007'
author:
- first_name: Thomas
  full_name: Werner, Thomas
  id: '89271'
  last_name: Werner
  orcid: 0000-0001-9025-3244
- first_name: Abdol
  full_name: Riahi, Abdol
  last_name: Riahi
- first_name: Heiko
  full_name: Schramm, Heiko
  last_name: Schramm
citation:
  ama: Werner T, Riahi A, Schramm H. Phosphonium Salt Catalyzed Addition of Diethylzinc
    to Aldehydes. <i>Synthesis</i>. 2011;2011(21):3482-3490. doi:<a href="https://doi.org/10.1055/s-0030-1260230">10.1055/s-0030-1260230</a>
  apa: Werner, T., Riahi, A., &#38; Schramm, H. (2011). Phosphonium Salt Catalyzed
    Addition of Diethylzinc to Aldehydes. <i>Synthesis</i>, <i>2011</i>(21), 3482–3490.
    <a href="https://doi.org/10.1055/s-0030-1260230">https://doi.org/10.1055/s-0030-1260230</a>
  bibtex: '@article{Werner_Riahi_Schramm_2011, title={Phosphonium Salt Catalyzed Addition
    of Diethylzinc to Aldehydes}, volume={2011}, DOI={<a href="https://doi.org/10.1055/s-0030-1260230">10.1055/s-0030-1260230</a>},
    number={21}, journal={Synthesis}, publisher={Georg Thieme Verlag KG}, author={Werner,
    Thomas and Riahi, Abdol and Schramm, Heiko}, year={2011}, pages={3482–3490} }'
  chicago: 'Werner, Thomas, Abdol Riahi, and Heiko Schramm. “Phosphonium Salt Catalyzed
    Addition of Diethylzinc to Aldehydes.” <i>Synthesis</i> 2011, no. 21 (2011): 3482–90.
    <a href="https://doi.org/10.1055/s-0030-1260230">https://doi.org/10.1055/s-0030-1260230</a>.'
  ieee: 'T. Werner, A. Riahi, and H. Schramm, “Phosphonium Salt Catalyzed Addition
    of Diethylzinc to Aldehydes,” <i>Synthesis</i>, vol. 2011, no. 21, pp. 3482–3490,
    2011, doi: <a href="https://doi.org/10.1055/s-0030-1260230">10.1055/s-0030-1260230</a>.'
  mla: Werner, Thomas, et al. “Phosphonium Salt Catalyzed Addition of Diethylzinc
    to Aldehydes.” <i>Synthesis</i>, vol. 2011, no. 21, Georg Thieme Verlag KG, 2011,
    pp. 3482–90, doi:<a href="https://doi.org/10.1055/s-0030-1260230">10.1055/s-0030-1260230</a>.
  short: T. Werner, A. Riahi, H. Schramm, Synthesis 2011 (2011) 3482–3490.
date_created: 2023-01-22T21:11:42Z
date_updated: 2025-11-10T09:40:42Z
department:
- _id: '35'
- _id: '2'
- _id: '657'
doi: 10.1055/s-0030-1260230
extern: '1'
intvolume: '      2011'
issue: '21'
keyword:
- T2
language:
- iso: eng
page: 3482-3490
publication: Synthesis
publication_identifier:
  issn:
  - 0039-7881
  - 1437-210X
publication_status: published
publisher: Georg Thieme Verlag KG
status: public
title: Phosphonium Salt Catalyzed Addition of Diethylzinc to Aldehydes
type: journal_article
user_id: '89271'
volume: 2011
year: '2011'
...