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  Catalytic synthesis of phenols with nitrous oxide

Le Vaillant, F., Mateos Calbet, A., González-Pelayo, S., Reijerse, E. J., Ni, S., Busch, J., et al. (2022). Catalytic synthesis of phenols with nitrous oxide. Nature, 604(7907), 677-683. doi:10.1038/s41586-022-04516-4.

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Le Vaillant, Franck1, Author              
Mateos Calbet, Ana1, Author              
González-Pelayo, Silvia1, Author
Reijerse, Edward J.2, Author
Ni, Shengyang1, Author              
Busch, Julia1, Author              
Cornella, Josep1, Author              
Affiliations:
1Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2466693              
2Max-Planck-Institut für Chemische Energiekonversion, Mülheim an der Ruhr, Germany, ou_persistent22              

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 Abstract: The development of catalytic chemical processes that enable the revalorization of nitrous oxide (N2O) is an attractive strategy to alleviate the environmental threat posed by its emissions1,2,3,4,5,6. Traditionally, N2O has been considered an inert molecule, intractable for organic chemists as an oxidant or O-atom transfer reagent, owing to the harsh conditions required for its activation (>150 °C, 50‒200 bar)7,8,9,10,11. Here we report an insertion of N2O into a Ni‒C bond under mild conditions (room temperature, 1.5–2 bar N2O), thus delivering valuable phenols and releasing benign N2. This fundamentally distinct organometallic C‒O bond-forming step differs from the current strategies based on reductive elimination and enables an alternative catalytic approach for the conversion of aryl halides to phenols. The process was rendered catalytic by means of a bipyridine-based ligands for the Ni centre. The method is robust, mild and highly selective, able to accommodate base-sensitive functionalities as well as permitting phenol synthesis from densely functionalized aryl halides. Although this protocol does not provide a solution to the mitigation of N2O emissions, it represents a reactivity blueprint for the mild revalorization of abundant N2O as an O source.

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Language(s): eng - English
 Dates: 2021-07-212022-02-042022-04-272022-04-28
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1038/s41586-022-04516-4
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Title: Nature
  Abbreviation : Nature
Source Genre: Journal
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Publ. Info: London : Nature Publishing Group
Pages: - Volume / Issue: 604 (7907) Sequence Number: - Start / End Page: 677 - 683 Identifier: ISSN: 0028-0836
CoNE: https://pure.mpg.de/cone/journals/resource/954925427238