4.7 Article

Synthesis of Unsymmetrical 2,6-Diarylanilines by Palladium Catalyzed C-H Bond Functionalization Methodology

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 10, Pages 5844-5850

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00659

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Funding

  1. Welch Foundation [E-0044]
  2. NIGMS [R01GM077635]

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3,5-Dimethylpyrazole was employed as a mono-d entate directing group for palladium-catalyzed ortho-sp(2) C-H arylation with aryl iodides. The reaction shows good functional group tolerance and outstanding selectivity for mono-orthoarylation. Ozonolysis of ortho-arylated arylpyrazoles gave acylated biphenylamines that were further arylated to afford unsymmetrically substituted 2,6-diarylacetanilides.

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