[{"page":"611-620","extern":"1","user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","date_updated":"2024-10-14T12:06:23Z","year":"2020","oa_version":"Preprint","date_published":"2020-08-01T00:00:00Z","issue":"8","publisher":"Springer Nature","type":"journal_article","day":"01","status":"public","article_type":"original","doi":"10.1038/s41929-020-0473-6","citation":{"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.","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>.","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>","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>","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.","short":"S. Gisbertz, S. Reischauer, B. Pieber, Nature Catalysis 3 (2020) 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>."},"article_processing_charge":"No","month":"08","title":"Overcoming limitations in dual photoredox/nickel-catalysed C–N cross-couplings due to catalyst deactivation","_id":"11979","intvolume":"         3","publication":"Nature Catalysis","author":[{"first_name":"Sebastian","full_name":"Gisbertz, Sebastian","last_name":"Gisbertz"},{"full_name":"Reischauer, Susanne","last_name":"Reischauer","first_name":"Susanne"},{"orcid":"0000-0001-8689-388X","last_name":"Pieber","full_name":"Pieber, Bartholomäus","first_name":"Bartholomäus","id":"93e5e5b2-0da6-11ed-8a41-af589a024726"}],"scopus_import":"1","main_file_link":[{"url":"https://doi.org/10.26434/chemrxiv.10298735","open_access":"1"}],"oa":1,"publication_identifier":{"eissn":["2520-1158"]},"language":[{"iso":"eng"}],"date_created":"2022-08-25T11:06:16Z","publication_status":"published","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."}],"quality_controlled":"1","volume":3}]