4.8 Article

Exploring the Reducing Ability of Organic Dye (Acr+-Mes) for Fluorination and Oxidation of Benzylic C(sp3)-H Bonds under Visible Light Irradiation

Journal

ORGANIC LETTERS
Volume 19, Issue 11, Pages 3009-3012

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01270

Keywords

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Funding

  1. Ministry of Science and Technology of China [2013CB834804, 2014CB239402, 2013CB834505]
  2. National Natural Science Foundation of China [21390404, 91427303]
  3. Strategic Priority Research Program of the Chinese Academy of Sciences [XDB17030400]
  4. Chinese Academy of Sciences

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The excellent oxidizing capability of acridinium-based organic dye (Acr(+)-Mes) is fully studied in photoredox catalysis. However, its reducing ability is always considered weak for organic transformation. The reducing ability of Acr(+)-Mes is developed by Selectfluor to achieve effective fluorination and oxidation of benzylic C(sp(3))-H bonds under visible light irradiation, which is not available for the direct use of oxidizing ability of excited Acr(+)-Mes. Mechanistic insights provided strong evidence for the oxidative quenching of Acr(+)-Mes.

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