{"year":"2020","quality_controlled":"1","abstract":[{"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.","lang":"eng"}],"issue":"8","oa":1,"user_id":"2DF688A6-F248-11E8-B48F-1D18A9856A87","volume":3,"main_file_link":[{"open_access":"1","url":"https://doi.org/10.26434/chemrxiv.10298735"}],"date_updated":"2023-02-21T10:10:09Z","intvolume":"         3","type":"journal_article","extern":"1","title":"Overcoming limitations in dual photoredox/nickel-catalysed C–N cross-couplings due to catalyst deactivation","article_type":"original","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>","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.","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>.","short":"S. Gisbertz, S. Reischauer, B. Pieber, Nature Catalysis 3 (2020) 611–620.","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>."},"doi":"10.1038/s41929-020-0473-6","oa_version":"Preprint","publisher":"Springer Nature","author":[{"last_name":"Gisbertz","first_name":"Sebastian","full_name":"Gisbertz, Sebastian"},{"full_name":"Reischauer, Susanne","first_name":"Susanne","last_name":"Reischauer"},{"first_name":"Bartholomäus","full_name":"Pieber, Bartholomäus","orcid":"0000-0001-8689-388X","id":"93e5e5b2-0da6-11ed-8a41-af589a024726","last_name":"Pieber"}],"article_processing_charge":"No","date_published":"2020-08-01T00:00:00Z","publication_status":"published","publication_identifier":{"eissn":["2520-1158"]},"month":"08","date_created":"2022-08-25T11:06:16Z","scopus_import":"1","publication":"Nature Catalysis","_id":"11979","day":"01","status":"public","language":[{"iso":"eng"}],"page":"611-620"}