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. 2018 May 18;83(10):5844-5850.
doi: 10.1021/acs.joc.8b00659. Epub 2018 May 8.

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

Se Hun Kwak  1 , Nurbey Gulia  1   2 , Olafs Daugulis  1
Affiliations

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

Se Hun Kwak et al. J Org Chem. .

Abstract

3,5-Dimethylpyrazole was employed as a monodentate directing group for palladium-catalyzed ortho-sp2 C-H arylation with aryl iodides. The reaction shows good functional group tolerance and outstanding selectivity for mono- ortho-arylation. Ozonolysis of ortho-arylated arylpyrazoles gave acylated biphenylamines that were further arylated to afford unsymmetrically substituted 2,6-diarylacetanilides.

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Conflict of interest statement

Notes

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1
Pyrazole-Directed C–H Arylation
Scheme 2
Scheme 2
Arylation with Aryl Iodides
Scheme 3
Scheme 3
Arylation of N-Arylpyrazoles
Scheme 4
Scheme 4
Directing Group Removal
Scheme 5
Scheme 5
Preparation of Unsymmetrically Substituted 2,6-Diarylanilines
See this image and copyright information in PMC

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