---
_id: '59619'
abstract:
- lang: eng
  text: "<jats:title>Abstract</jats:title><jats:p>A frustrated Lewis pair‐catalyzed
    hydroboration of aromatic and aliphatic nitriles was developed. The catalyst provides
    the primary amines in high yields of 77–99% with catalyst loading as low as 2 mol%.
    The reaction displays high functional group tolerance towards esters, amides,
    nitro groups and aliphatic halides. The addition of the diborylated amines to
    ethyl 3‐phenylpropiolate proceeds with Z‐selectivity with d.r. of &gt;99:1 in
    77–90% yield over two steps. The reaction mechanism was investigated by control
    and computational experiments.</jats:p><jats:p><jats:boxed-text content-type=\"graphic\"
    position=\"anchor\"><jats:graphic xmlns:xlink=\"http://www.w3.org/1999/xlink\"
    mimetype=\"image/png\" position=\"anchor\" specific-use=\"enlarged-web-image\"
    xlink:href=\"graphic/adsc202200525-toc-0001-m.png\"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:boxed-text>\r\n</jats:p>"
author:
- first_name: Benedikt
  full_name: Sieland, Benedikt
  last_name: Sieland
- first_name: Axel
  full_name: Hoppe, Axel
  id: '62844'
  last_name: Hoppe
- first_name: Arne J.
  full_name: Stepen, Arne J.
  last_name: Stepen
- first_name: Jan
  full_name: Paradies, Jan
  id: '53339'
  last_name: Paradies
  orcid: 0000-0002-3698-668X
citation:
  ama: 'Sieland B, Hoppe A, Stepen AJ, Paradies J. Frustrated Lewis Pair‐Catalyzed
    Hydroboration of Nitriles: FLP Versus Borenium Catalysis. <i>Advanced Synthesis
    &#38;amp; Catalysis</i>. 2022;364(18):3143-3148. doi:<a href="https://doi.org/10.1002/adsc.202200525">10.1002/adsc.202200525</a>'
  apa: 'Sieland, B., Hoppe, A., Stepen, A. J., &#38; Paradies, J. (2022). Frustrated
    Lewis Pair‐Catalyzed Hydroboration of Nitriles: FLP Versus Borenium Catalysis.
    <i>Advanced Synthesis &#38;amp; Catalysis</i>, <i>364</i>(18), 3143–3148. <a href="https://doi.org/10.1002/adsc.202200525">https://doi.org/10.1002/adsc.202200525</a>'
  bibtex: '@article{Sieland_Hoppe_Stepen_Paradies_2022, title={Frustrated Lewis Pair‐Catalyzed
    Hydroboration of Nitriles: FLP Versus Borenium Catalysis}, volume={364}, DOI={<a
    href="https://doi.org/10.1002/adsc.202200525">10.1002/adsc.202200525</a>}, number={18},
    journal={Advanced Synthesis &#38;amp; Catalysis}, publisher={Wiley}, author={Sieland,
    Benedikt and Hoppe, Axel and Stepen, Arne J. and Paradies, Jan}, year={2022},
    pages={3143–3148} }'
  chicago: 'Sieland, Benedikt, Axel Hoppe, Arne J. Stepen, and Jan Paradies. “Frustrated
    Lewis Pair‐Catalyzed Hydroboration of Nitriles: FLP Versus Borenium Catalysis.”
    <i>Advanced Synthesis &#38;amp; Catalysis</i> 364, no. 18 (2022): 3143–48. <a
    href="https://doi.org/10.1002/adsc.202200525">https://doi.org/10.1002/adsc.202200525</a>.'
  ieee: 'B. Sieland, A. Hoppe, A. J. Stepen, and J. Paradies, “Frustrated Lewis Pair‐Catalyzed
    Hydroboration of Nitriles: FLP Versus Borenium Catalysis,” <i>Advanced Synthesis
    &#38;amp; Catalysis</i>, vol. 364, no. 18, pp. 3143–3148, 2022, doi: <a href="https://doi.org/10.1002/adsc.202200525">10.1002/adsc.202200525</a>.'
  mla: 'Sieland, Benedikt, et al. “Frustrated Lewis Pair‐Catalyzed Hydroboration of
    Nitriles: FLP Versus Borenium Catalysis.” <i>Advanced Synthesis &#38;amp; Catalysis</i>,
    vol. 364, no. 18, Wiley, 2022, pp. 3143–48, doi:<a href="https://doi.org/10.1002/adsc.202200525">10.1002/adsc.202200525</a>.'
  short: B. Sieland, A. Hoppe, A.J. Stepen, J. Paradies, Advanced Synthesis &#38;amp;
    Catalysis 364 (2022) 3143–3148.
date_created: 2025-04-22T06:01:56Z
date_updated: 2025-04-22T06:12:05Z
department:
- _id: '389'
doi: 10.1002/adsc.202200525
intvolume: '       364'
issue: '18'
keyword:
- hydroboration
- nitrile
- amine
- frustrated Lewis pair
- density functional theory
language:
- iso: eng
main_file_link:
- open_access: '1'
  url: https://advanced.onlinelibrary.wiley.com/doi/10.1002/adsc.202200525
oa: '1'
page: 3143-3148
publication: Advanced Synthesis &amp; Catalysis
publication_identifier:
  issn:
  - 1615-4150
  - 1615-4169
publication_status: published
publisher: Wiley
quality_controlled: '1'
status: public
title: 'Frustrated Lewis Pair‐Catalyzed Hydroboration of Nitriles: FLP Versus Borenium
  Catalysis'
type: journal_article
user_id: '62844'
volume: 364
year: '2022'
...