Palladium-Catalyzed Direct α‑C(sp3) Heteroarylation of Ketones under Microwave Irradiation

Heteroaryl compounds are valuable building blocks in medicinal chemistry and chemical industry. A palladium-catalyzed direct α-C­(sp3) heteroarylation of ketones under microwave irradiation is developed and reported in this study. Under optimized conditions, twenty-eight (28) heteroarylated ketones...

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Veröffentlicht in:Journal of organic chemistry 2019-06, Vol.84 (12), p.7652-7663
Hauptverfasser: Quillen, Andrew, Nguyen, Quynh, Neiser, Matthew, Lindsay, Kara, Rosen, Alexander, Ramirez, Stephen, Costan, Stefana, Johnson, Nathan, Do, Thuy Donna, Rodriguez, Oscar, Rivera, Diego, Atesin, Abdurrahman, Ateşin, Tülay Aygan, Ma, Lili
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Sprache:eng
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Zusammenfassung:Heteroaryl compounds are valuable building blocks in medicinal chemistry and chemical industry. A palladium-catalyzed direct α-C­(sp3) heteroarylation of ketones under microwave irradiation is developed and reported in this study. Under optimized conditions, twenty-eight (28) heteroarylated ketones were prepared in this study to demonstrate the substrate scope of this reaction. The ground-state optimized structure of Pd(0) active catalyst with 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos) in toluene, and the products of its reaction with 3-bromopyridine and acetophenone were studied using all-atom density functional theory. This study provided insightful information for palladium catalytic system design to generate heteroaryl compounds.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00446