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

Se Hun Kwak; Nurbey Gulia; Olafs Daugulis

doi:10.1021/acs.joc.8b00659

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

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

Authors

Se Hun Kwak¹, Nurbey Gulia^{1

2}, Olafs Daugulis¹

Affiliations

¹ Department of Chemistry , University of Houston , Houston , Texas 77204-5003 , United States.
² Department of Chemistry , University of Wrocław , 14 F. Joliot-Curie , 50-383 Wrocław , Poland.

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.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Aniline Compounds / chemical synthesis*
Aniline Compounds / chemistry
Catalysis
Molecular Structure
Organometallic Compounds / chemistry*
Ozone / chemistry
Palladium / chemistry*

Substances

Aniline Compounds
Organometallic Compounds
Palladium
Ozone

Grants and funding

R01 GM077635/GM/NIGMS NIH HHS/United States