4.6 Article

Quinone-Mediated Trifluoromethylation of Arenes and Heteroarenes with Visible Light

Journal

ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 5, Issue 1, Pages 334-341

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.6b01682

Keywords

Quinone; MnO2; Photoinduced; Trifluoromethylation; Radical

Funding

  1. National Nature Science Foundation of China [21077023]
  2. National Basic Research Program of China [2014CB239303]
  3. Natural Science Foundation of Fujian Province of China [2015J01046]
  4. Independent Research Project of State Key Laboratory of Photocatalysis on Energy and Environment [2014B01]

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The trifluoromethyl group can significantly influence the physical and chemical properties of organic molecules, thereby increasing their applications in the fields of pharmaceuticals, agro-chemicals, and organic materials. An efficient visible-light-promoted method for the direct trifluoromethylation of arenes and heteroarenes has been developed using inexpensive CF3SO2Na as the CF3 radical source and naturally ubiquitous quinones as oxidants. The regeneration of quinones was successfully realized by using a MnO2-fixed bed. This operationally simple methodology not only provides an access to a wide variety of CF3-containing building blocks from simple starting materials but also exhibits potential applications on a larger scale synthesis utilizing visible light energy.

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