4.7 Article

Metal-Free Trifluoromethylthiolation of Arylazo Sulfones

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 1, Pages 1292-1299

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02669

Keywords

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Funding

  1. National Natural Science Foundation of China [21572158]
  2. Tianjin Natural Science Foundation [18JCQNJC76600]

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This protocol for the synthesis of aryl trifluoromethyl thioethers under visible-light-driven conditions does not require the use of photocatalysts or metal catalysts. It utilizes the unique properties of arylazo sulfones and S-trifluoromethyl arylsulfonothioates as precursors, making the procedure easy to handle.
A visible-light-driven protocol for the synthesis of aryl trifluoromethyl thioethers under photocatalyst- and metal-free conditions has been pursued. The procedure exploits the peculiar properties of arylazo sulfones (having electron-rich or electronpoor substituents on the (hetero)aromatic ring) as photochemical precursors of aryl radicals and S-trifluoromethyl arylsulfonothioates as easy-to-handle trifluoromethylthiolating agents.

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