Helical Carbenium Ion: A Versatile Organic Photoredox Catalyst for Red-Light-Mediated Reactions

Liangyong Mei, José M. Veleta, Thomas L. Gianetti

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

Red light has the advantages of low energy, less health risks, and high penetration depth through various media. Herein, a helical carbenium ion (N,N′-di-n-propyl-1,13-dimethoxyquinacridinium (nPr-DMQA+) tetrafluoroborate) has been used as an organic photoredox catalyst for photoreductions and photooxidations in the presence of red light (λmax = 640 nm). It has catalyzed red-light-mediated dual transition-metal/photo-redox-catalyzed C-H arylation and intermolecular atom-transfer radical addition through oxidative quenching. Moreover, its potential in photooxidation catalysis has also been demonstrated by successful applications in red-light-induced aerobic oxidative hydroxylation of arylboronic acids and benzylic C(sp3)-H oxygenation through reductive quenching. Thus, a versatile organic photoredox catalyst (helical carbenium ion) for red-light-mediated photoredox reactions has been developed.

Original languageEnglish (US)
Pages (from-to)12056-12061
Number of pages6
JournalJournal of the American Chemical Society
Volume142
Issue number28
DOIs
StatePublished - Jul 15 2020

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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