Visible Light Induced Difluoroalkylation of 8-Aminoquinoline Derivatives
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O621.3;

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    Abstract:

    A copper-catalyzed visible light induced difluoroalkylation reaction of 8-aminoquinoline derivatives at the C5- position was developed at room temperature. The C—C coupling reaction between 8-aminoquinoline derivatives and free radicals of ethyl difluoroacetate produced by ethyl difluorobromoacetate was carried out with blue LED as light source, fac-Tris[2-(2-pyridinyl)phenyl] iridium(Ⅲ) complexes (fac-Ir(ppy)3) as photosensitizer. Fifteen difluoroalkylated 8-aminoquinoline derivatives (Ⅲa~Ⅲo) at the C5 position were synthesized in the presence of a catalytic amount of cuprous iodide. These products were characterized by 1HNMR, 13HNMR, FTIR, and HR-MS. The conversion rates of starting materials were50%~90%, and yields of products was in the range from 21% to 58%. The reaction conditions are mild, and the substrates containing halogen, thioether, and cyan functional groups can react. Free radical scavenger2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) could capture free radicals of ethyl difluoroacetate, indicating that the reaction process may undergo free radical single electron transfer.

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History
  • Received:February 18,2020
  • Revised:April 13,2020
  • Adopted:April 14,2020
  • Online: June 08,2020
  • Published:
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