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

Authors

Andrew Quillen
Quynh Nguyen
Matthew Neiser
Kara Lindsay
Alexander Rosen
Stephen Ramirez
Stefana Costan
Oscar Rodriguez, The University of Texas Rio Grande Valley
Diego Rivera, The University of Texas Rio Grande Valley
Abdurrahman Atesin, The University of Texas Rio Grande Valley
Tülay A. Ateşin, The University of Texas Rio Grande Valley

Document Type

Article

Publication Date

4-19-2019

Abstract

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.

Comments

© 2019 American Chemical Society RIGHTS & PERMISSIONS

Recommended Citation

Quillen, Andrew, et al. "Palladium-Catalyzed direct α-C (sp3) heteroarylation of ketones under microwave irradiation." The Journal of Organic Chemistry 84.12 (2019): 7652-7663. https://doi.org/10.1021/acs.joc.9b00446

Publication Title

J. Org. Chem.

DOI

10.1021/acs.joc.9b00446