4.8 Article

Iron-Catalyzed Ortho-Allylation of Aromatic Carboxamides with Allyl Ethers

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 47, Pages 17755-17757

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja4106368

Keywords

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Funding

  1. MEXT (KAKENHI) [22000008, 23750100, 25105711]
  2. Japan Society for the Promotion of Science for Young Scientists [23-8207]
  3. Grants-in-Aid for Scientific Research [11J08207, 22000008, 25105711] Funding Source: KAKEN

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Arenes possessing an N-(quinolin-8-yl)-amide directing group are ortho-allylated with allyl phenyl ether in the presence of an iron/diphosphine catalyst and an organometallic base at 50-70 degrees C. The reaction proceeds via fast iron-catalyzed C-H activation, followed by reaction of the resulting iron intermediate with the allyl ether in gamma-selective fashion.

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