4.7 Article

Copper-Catalyzed Regioselective C-H Sulfonyloxylation of Electron-Rich Arenes with p-Toluenesulfonic Acid and Sulfonyloxylation of Aryl(mesityl)iodonium Sulfonates

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 6, Pages 3094-3101

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00081

Keywords

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Funding

  1. National Natural Science Foundation of China [21202109]
  2. Sichuan Provincial Department of Education [14ZB0028]
  3. Sichuan Normal University [16ZP10, DJ2016-44, xyz2016-4-34]

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Copper-catalyzed regioselective C-H sulfonyloxylation of electron-rich arenes with p-toluenesulfonic acid has been developed. Electron-rich benzene derivatives and heteroarenes can undergo this C-H sulfonyloxylation reaction to generate aryl tosylates. Furthermore, sulfonyloxylation of aryl(mesityl)iodonium sulfonates has also been investigated. Both aryl(mesityl)iodonium tosylates and triflates can react smoothly to get aryl sulfonates. The formed aryl sulfonates can be converted to phenols, as well as used as good partners of cross-coupling reactions. [GRAPHICS]

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