Palladium‐Catalyzed Acyl Suzuki–Miyaura Coupling from Carboxylic Acids In Situ Activated by HATU: An Efficient Way to Ketones Laid by Nitrogen Coordination

A palladium‐catalyzed acyl Suzuki–Miyaura coupling between carboxylic acids and organoboronic acids has been developed, employing hexafluorophosphate azabenzotriazole tetramethyl uronium as an in situ activator. Using Pd 2 (dba) 3 /PCy 3 as the catalyst and K 2 CO 3 as the base, the reaction accommodates a broad range of both aliphatic and aromatic carboxylic acids. Controlled experiments and density functional theory calculations reveal that the pyridine nitrogen plays a critical role in the catalytic cycle.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-09-25
DOI
https://doi.org/10.1002/ejoc.202500799
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
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Palladium‐Catalyzed Acyl Suzuki–Miyaura Coupling from Carboxylic Acids In Situ Activated by HATU: An Efficient Way to Ketones Laid by Nitrogen Coordination

Chaoren Shen, Mengmeng Zhao, Wanfang Li, Junyu Pan et al.
European Journal of Organic Chemistry
Catalytic Cross-Coupling Reactions
article

Palladium‐Catalyzed Acyl Suzuki–Miyaura Coupling from Carboxylic Acids In Situ Activated by HATU: An Efficient Way to Ketones Laid by Nitrogen Coordination

Chaoren Shen, Mengmeng Zhao, Wanfang Li, Junyu Pan, Shuo Zhang, Hui You, Daming Liu
article en

Abstract

A palladium‐catalyzed acyl Suzuki–Miyaura coupling between carboxylic acids and organoboronic acids has been developed, employing hexafluorophosphate azabenzotriazole tetramethyl uronium as an in situ activator. Using Pd 2 (dba) 3 /PCy 3 as the catalyst and K 2 CO 3 as the base, the reaction accommodates a broad range of both aliphatic and aromatic carboxylic acids. Controlled experiments and density functional theory calculations reveal that the pyridine nitrogen plays a critical role in the catalytic cycle.

European Journal of Organic ChemistryVol. 28(43)
University of Shanghai for Science and Technology (CN), Linyi University (CN), East China Normal University (CN)
Openalex Percentile: Top 80%
Catalytic Cross-Coupling Reactions
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