---
_id: '11979'
abstract:
- lang: eng
  text: Dual photoredox/nickel-catalysed C–N cross-couplings suffer from low yields
    for electron-rich aryl halides. The formation of catalytically inactive nickel-black
    is responsible for this limitation and causes severe reproducibility issues. Here,
    we demonstrate that catalyst deactivation can be avoided by using a carbon nitride
    photocatalyst. The broad absorption of the heterogeneous photocatalyst enables
    wavelength-dependent control of the rate of reductive elimination to prevent nickel-black
    formation during the coupling of cyclic, secondary amines and aryl halides. A
    second approach, which is applicable to a broader set of electron-rich aryl halides,
    is to run the reactions at high concentrations to increase the rate of oxidative
    addition. Less nucleophilic, primary amines can be coupled with electron-rich
    aryl halides by stabilizing low-valent nickel intermediates with a suitable additive.
    The developed protocols enable reproducible, selective C–N cross-couplings of
    electron-rich aryl bromides and can also be applied for electron-poor aryl chlorides.
article_processing_charge: No
article_type: original
author:
- first_name: Sebastian
  full_name: Gisbertz, Sebastian
  last_name: Gisbertz
- first_name: Susanne
  full_name: Reischauer, Susanne
  last_name: Reischauer
- first_name: Bartholomäus
  full_name: Pieber, Bartholomäus
  id: 93e5e5b2-0da6-11ed-8a41-af589a024726
  last_name: Pieber
  orcid: 0000-0001-8689-388X
citation:
  ama: Gisbertz S, Reischauer S, Pieber B. Overcoming limitations in dual photoredox/nickel-catalysed
    C–N cross-couplings due to catalyst deactivation. <i>Nature Catalysis</i>. 2020;3(8):611-620.
    doi:<a href="https://doi.org/10.1038/s41929-020-0473-6">10.1038/s41929-020-0473-6</a>
  apa: Gisbertz, S., Reischauer, S., &#38; Pieber, B. (2020). Overcoming limitations
    in dual photoredox/nickel-catalysed C–N cross-couplings due to catalyst deactivation.
    <i>Nature Catalysis</i>. Springer Nature. <a href="https://doi.org/10.1038/s41929-020-0473-6">https://doi.org/10.1038/s41929-020-0473-6</a>
  chicago: Gisbertz, Sebastian, Susanne Reischauer, and Bartholomäus Pieber. “Overcoming
    Limitations in Dual Photoredox/Nickel-Catalysed C–N Cross-Couplings Due to Catalyst
    Deactivation.” <i>Nature Catalysis</i>. Springer Nature, 2020. <a href="https://doi.org/10.1038/s41929-020-0473-6">https://doi.org/10.1038/s41929-020-0473-6</a>.
  ieee: S. Gisbertz, S. Reischauer, and B. Pieber, “Overcoming limitations in dual
    photoredox/nickel-catalysed C–N cross-couplings due to catalyst deactivation,”
    <i>Nature Catalysis</i>, vol. 3, no. 8. Springer Nature, pp. 611–620, 2020.
  ista: Gisbertz S, Reischauer S, Pieber B. 2020. Overcoming limitations in dual photoredox/nickel-catalysed
    C–N cross-couplings due to catalyst deactivation. Nature Catalysis. 3(8), 611–620.
  mla: Gisbertz, Sebastian, et al. “Overcoming Limitations in Dual Photoredox/Nickel-Catalysed
    C–N Cross-Couplings Due to Catalyst Deactivation.” <i>Nature Catalysis</i>, vol.
    3, no. 8, Springer Nature, 2020, pp. 611–20, doi:<a href="https://doi.org/10.1038/s41929-020-0473-6">10.1038/s41929-020-0473-6</a>.
  short: S. Gisbertz, S. Reischauer, B. Pieber, Nature Catalysis 3 (2020) 611–620.
date_created: 2022-08-25T11:06:16Z
date_published: 2020-08-01T00:00:00Z
date_updated: 2023-02-21T10:10:09Z
day: '01'
doi: 10.1038/s41929-020-0473-6
extern: '1'
intvolume: '         3'
issue: '8'
language:
- iso: eng
main_file_link:
- open_access: '1'
  url: https://doi.org/10.26434/chemrxiv.10298735
month: '08'
oa: 1
oa_version: Preprint
page: 611-620
publication: Nature Catalysis
publication_identifier:
  eissn:
  - 2520-1158
publication_status: published
publisher: Springer Nature
quality_controlled: '1'
scopus_import: '1'
status: public
title: Overcoming limitations in dual photoredox/nickel-catalysed C–N cross-couplings
  due to catalyst deactivation
type: journal_article
user_id: 2DF688A6-F248-11E8-B48F-1D18A9856A87
volume: 3
year: '2020'
...