JOURNAL ARTICLE

Regiodivergent C−H Acylation of Arenes by Switching from Ionic‐ to Radical‐Type Chemistry Using NHC Catalysis.

  • Published In: Angewandte Chemie International Edition, 2023, v. 62, n. 27. P. 1 1 of 3

  • Database: Academic Search Ultimate 2 of 3

  • Authored By: Reimler, Jannik; Yu, Xiao‐Ye; Spreckelmeyer, Nico; Daniliuc, Constantin G.; Studer, Armido 3 of 3

Abstract

The Friedel–Crafts acylation reaction, which belongs to the class of electrophilic aromatic substitutions is a highly valuable and versatile reaction in synthesis. Regioselectivity is predictable and determined by electronic as well as steric factors of the (hetero)arene substrate. Herein, a radical approach for the acylation of arenes and heteroarenes is presented. C−H acylation is achieved through mild cooperative photoredox/NHC radical catalysis with the cross‐coupling of an arene radical cation with an NHC‐bound ketyl radical as a key step. As compared to the classical Friedel–Crafts acylation, a regiodivergent outcome is observed upon switching from the ionic to the radical mode. In these divergent reactions, aroyl fluorides act as the acylation reagents in both the ionic as well as the radical process. [ABSTRACT FROM AUTHOR]

Additional Information

  • Source:Angewandte Chemie International Edition. 2023/07, Vol. 62, Issue 27, p1
  • Document Type:Article
  • Subject Area:Chemistry
  • Publication Date:2023
  • ISSN:1433-7851
  • DOI:10.1002/anie.202303222
  • Accession Number:164586679
  • Copyright Statement:Copyright of Angewandte Chemie International Edition is the property of Wiley-Blackwell and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

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