@article{11979,
  abstract     = {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.},
  author       = {Gisbertz, Sebastian and Reischauer, Susanne and Pieber, Bartholomäus},
  issn         = {2520-1158},
  journal      = {Nature Catalysis},
  number       = {8},
  pages        = {611--620},
  publisher    = {Springer Nature},
  title        = {{Overcoming limitations in dual photoredox/nickel-catalysed C–N cross-couplings due to catalyst deactivation}},
  doi          = {10.1038/s41929-020-0473-6},
  volume       = {3},
  year         = {2020},
}