Fluorine-Based Oxidant Enables Room-Temperature Pd-Catalyzed C–H Arylation with Boronic Acids

The biaryl motif is important in many fields within chemistry and the life sciences. Thus, better strategies to forge aryl-aryl bonds are valuable. Herein, we report conditions permitting the room temperature arylation of <i>N</i>-aryl amide substrates, using ubiquitous aryl boronic acid reagents. Critical to the success of this method is the use of Selectfluor as a sustainable alternative oxidant to silver-based additives and the deployment of a bulky QuinOx ligand supporting the palladium catalyst.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-03-13
DOI
https://doi.org/10.1021/acs.joc.4c03106
Citations
2
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.87

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article

Fluorine-Based Oxidant Enables Room-Temperature Pd-Catalyzed C–H Arylation with Boronic Acids

Nicholas McDonald, Erik A. Romero, Delphine Pichon
2 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
1.87
article

Fluorine-Based Oxidant Enables Room-Temperature Pd-Catalyzed C–H Arylation with Boronic Acids

Nicholas McDonald, Erik A. Romero, Delphine Pichon
article en
2 citations

Abstract

The biaryl motif is important in many fields within chemistry and the life sciences. Thus, better strategies to forge aryl-aryl bonds are valuable. Herein, we report conditions permitting the room temperature arylation of <i>N</i>-aryl amide substrates, using ubiquitous aryl boronic acid reagents. Critical to the success of this method is the use of Selectfluor as a sustainable alternative oxidant to silver-based additives and the deployment of a bulky QuinOx ligand supporting the palladium catalyst.

The Journal of Organic ChemistryVol. 90(11)
University of California San Diego (US)
University of California, San Diego
Openalex Percentile: Top 17%
Catalytic C–H Functionalization Methods
1.87
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