Redox Inversion: A Radical Analogue of Umpolung Reactivity for Base- and Metal-Free Catalytic C(sp3)-C(sp3) Coupling

Chris M. Seong, Annabel Q. Ansel, Courtney C. Roberts

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The construction of alkyl-alkyl bonds is a powerful tool in organic synthesis. Redox inversion, defined as switching the donor/acceptor profile of a functional group to its acceptor/donor profile, is used for C(sp3)-C(sp3) coupling. We report a photocatalytic coupling of carboxylic acids to form bibenzyls through a radical-radical coupling. Mechanistic insight is gained through control reactions. This unexplored redox-opposite relationship between a carboxylic acid and its redox-active ester is implemented in catalysis.

Original languageEnglish (US)
Pages (from-to)3935-3940
Number of pages6
JournalJournal of Organic Chemistry
Volume88
Issue number6
DOIs
StatePublished - Mar 17 2023
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2023 American Chemical Society

PubMed: MeSH publication types

  • Journal Article

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