Palladium-Catalyzed\nTandem Reaction of β‑Ketonitriles\nwith Arylboronic Acids and Dimethyl Sulfoxide: Application to Multicomponent\nSynthesis of Poly-Substituted Pyridines

The\nPd-catalyzed multicomponent tandem reaction of β-ketonitriles,\narylboronic acids and DMSO was efficiently developed, enabling access\nto a variety of poly substituted pyridines. The protocol shows excellent\nchemoselectivity, generating nicotinonitriles or symmetrical tetrasubstituted\npyridines under different conditions by tandem cyclization of enaminone\nintermediates with β-ketonitriles or enolates, respectively,\nand does not require extra ammonias. This method boasts notable advantages,\nsuch as the use of commercially available or easily prepared substrates,\nsimple conditions, a broad substrate scope, and good functional group\ntolerance.

Publication Details

Journal
Figshare
Published
2025-01-09
DOI
https://doi.org/10.1021/acs.joc.4c02778.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Palladium-Catalyzed\nTandem Reaction of β‑Ketonitriles\nwith Arylboronic Acids and Dimethyl Sulfoxide: Application to Multicomponent\nSynthesis of Poly-Substituted Pyridines

Figshare
Catalytic C–H Functionalization Methods
article

Palladium-Catalyzed\nTandem Reaction of β‑Ketonitriles\nwith Arylboronic Acids and Dimethyl Sulfoxide: Application to Multicomponent\nSynthesis of Poly-Substituted Pyridines

article en

Abstract

The\nPd-catalyzed multicomponent tandem reaction of β-ketonitriles,\narylboronic acids and DMSO was efficiently developed, enabling access\nto a variety of poly substituted pyridines. The protocol shows excellent\nchemoselectivity, generating nicotinonitriles or symmetrical tetrasubstituted\npyridines under different conditions by tandem cyclization of enaminone\nintermediates with β-ketonitriles or enolates, respectively,\nand does not require extra ammonias. This method boasts notable advantages,\nsuch as the use of commercially available or easily prepared substrates,\nsimple conditions, a broad substrate scope, and good functional group\ntolerance.

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Catalytic C–H Functionalization Methods
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