Palladium-Catalyzed Tandem Reaction of β-Ketonitriles with Arylboronic Acids and Dimethyl Sulfoxide: Application to Multicomponent Synthesis of Poly-Substituted Pyridines

The Pd-catalyzed multicomponent tandem reaction of β-ketonitriles, arylboronic acids and DMSO was efficiently developed, enabling access to a variety of poly substituted pyridines. The protocol shows excellent chemoselectivity, generating nicotinonitriles or symmetrical tetrasubstituted pyridines under different conditions by tandem cyclization of enaminone intermediates with β-ketonitriles or enolates, respectively, and does not require extra ammonias. This method boasts notable advantages, such as the use of commercially available or easily prepared substrates, simple conditions, a broad substrate scope, and good functional group tolerance.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-01-09
DOI
https://doi.org/10.1021/acs.joc.4c02778
Citations
6
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
5.62

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article

Palladium-Catalyzed Tandem Reaction of β-Ketonitriles with Arylboronic Acids and Dimethyl Sulfoxide: Application to Multicomponent Synthesis of Poly-Substituted Pyridines

Weiping Han, Miaochang Liu, Honggui Zhou, Jiuxi Chen et al.
6 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
5.62
article

Palladium-Catalyzed Tandem Reaction of β-Ketonitriles with Arylboronic Acids and Dimethyl Sulfoxide: Application to Multicomponent Synthesis of Poly-Substituted Pyridines

Weiping Han, Miaochang Liu, Honggui Zhou, Jiuxi Chen, Min Liu, Yifei Li, Ge Zeng, Renhao Li, Shi-Yan Wang
article en
6 citations

Abstract

The Pd-catalyzed multicomponent tandem reaction of β-ketonitriles, arylboronic acids and DMSO was efficiently developed, enabling access to a variety of poly substituted pyridines. The protocol shows excellent chemoselectivity, generating nicotinonitriles or symmetrical tetrasubstituted pyridines under different conditions by tandem cyclization of enaminone intermediates with β-ketonitriles or enolates, respectively, and does not require extra ammonias. This method boasts notable advantages, such as the use of commercially available or easily prepared substrates, simple conditions, a broad substrate scope, and good functional group tolerance.

The Journal of Organic ChemistryVol. 90(3)
Wenzhou University (CN), Wenzhou Medical University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Zhejiang Province
Clean water and sanitation
Openalex Percentile: Top 5%
Catalytic C–H Functionalization Methods
5.62
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Palladium-Catalyzed Tandem Reaction of β-Ketonitriles with Arylboronic Acids and Dimethyl Sulfoxide: Application to Multicomponent Synthesis of Poly-Substituted Pyridines — Weiping Han, Miaochang Liu, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS