Visible-Light-Mediated Deaminative Three-Component Dicarbofunctionalization of Styrenes with Benzylic Radicals

Felix J.R. Klauck, Hyung Yoon, Michael J. James, Mark Lautens*, Frank Glorius

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The visible-light-mediated three-component dicarbofunctionalization of styrenes using simple benzylic radicals is described. Notably, this work describes a rare example of undirected dicarbofunctionalization using unsubstituted benzyl radicals. Key to the success of this strategy was the rational design and use of benzylic pyridinium salts as radical precursors. Using this approach, abundant styrenes, electron-rich heterocycles, and benzylic amines were combined to rapidly afford a number of densely functionalized 1,1-diarylalkanes. A dipeptide-derived pyridinium salt was applied in this transformation, which resembles a visible-light-mediated deaminative generation of radicals from peptides.

Original languageEnglish
Pages (from-to)236-241
Number of pages6
JournalACS Catalysis
Volume9
Issue number1
Early online date26 Nov 2018
DOIs
Publication statusPublished - 4 Jan 2019

Bibliographical note

© 2018 American Chemical Society. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

Keywords

  • deamination
  • dicarbofunctionalization
  • photoredox catalysis
  • redox-active
  • visible-light

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