4.7 Article

Copper-catalyzed Meerwein carboarylation of alkenes with anilines to form 3-benzyl-3-alkyloxindole

Journal

SCIENCE CHINA-CHEMISTRY
Volume 58, Issue 4, Pages 684-688

Publisher

SCIENCE PRESS
DOI: 10.1007/s11426-014-5158-z

Keywords

radical reaction; C-H cyclization; Meerwein arylation; oxindole; copper-catalyzed

Funding

  1. National Natural Science Foundation of China [21462017]
  2. China Posdoctoral Science Foundation [2014M560649]
  3. Scientific Research Fund of Hunan Provincial Education Department [13B094]
  4. Fund of Science and Technology Innovation and Entrepreneur for Hunan Young Talents
  5. Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry

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A simple and direct route for double C-C bond formation by copper-catalyzed Meerwein carboarylation process has been developed. In the presence of CuI (5 mol%), tert-butyl nitrite and anilines, a wide variety of N-arylacrylamides underwent tandem Meerwein arylation/C-H cyclization to produce pharmaceutically important 3-benzyl-3-alkyloxindole in moderate to good yield.

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