4.7 Article

Iridium( I)-Catalyzed Direct C-H Bond Alkylation of the C-7 Position of Indolines with Alkenes

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 356, Issue 5, Pages 929-933

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300917

Keywords

alkenes; alkylation; CH functionalization; iridium catalysts; N-substituted indolines

Funding

  1. MEXT
  2. JST
  3. ACT-C
  4. Grants for Excellent Graduate School (Practical Chemical Wisdom), Waseda University, MEXT, Japan
  5. Grants-in-Aid for Scientific Research [25105748] Funding Source: KAKEN

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A cationic iridium-catalyzed C-7 alkylation of N-substituted indoline derivatives with various alkenes has been developed. A variety of 7-alkylindolines were obtained in moderate to high yields. This protocol relies on the use of the carbonyl group on the nitrogen atom of indoline as a directing group and it is potentially applicable to the large-scale synthesis of 7-alkylindoles.

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