4.7 Article

Cp*Rh(III)-Catalyzed Directed C-H Methylation and Arylation of Quinoline N-Oxides at the C-8 Position

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 17, Pages 3029-3034

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700484

Keywords

Quinoline N-Oxides; C-H Methylation; Rhodium

Funding

  1. National Natural Science Foundation of China [81620108027, 21632008, 91229204, 81220108025, 81602975]
  2. Major Project of Chinese National Programs for Fundamental Research and Development [2015CB910304]
  3. National S&T Major Projects [2014ZX09507002-001]

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Herein, we report a Cp*Rh(III)-catalyzed directed C-H methylation of quinoline N-oxides at the C-8 position using commercially available organotrifluoroborates as reagents. This method features perfect regioselectivity, relatively mild reaction conditions, and diverse functional group tolerance with good to excellent yields. Additionally, direct C-8 arylated quinoline N-oxides products could also be obtained under the same conditions. Preliminary mechanistic experiments were conducted and a possible mechanism was proposed.

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