4.6 Article

Protolytic defluorination of trifluoromethyl-substituted arenes

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 12, Pages 4545-4549

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob01276a

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Funding

  1. National Science Foundation [CHE-0749907]
  2. NIH-National Institute of General Medical Sciences [GM085736-01A1]
  3. NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R15GM085736] Funding Source: NIH RePORTER

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A series of trifluoromethyl-substituted arenes were studied in their reactions with Bronsted superacids. The products from these reactions suggest the formation of reactive electrophiles, such as carbocations, acylium cations or equivalent electrophilic species. As such, Friedel-Crafts-type reactions occur between these species and arene nucleophiles. NMR studies were done, and the results suggest the formation of an acyl group from the trifluoromethyl groups in the superacid.

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