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Updated: Jun 23, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Synthesis of C-Heteroaryl Nucleosides via Deoxygenative Arylation
Jordan Y Artzy1, Wenbin Liu1, Yunyi Wang2
1Department of Process Research & Development, Merck & Co., Inc., West Point, Pennsylvania 19486, United States.
None:
C-Aryl nucleosides are medicinally valuable due to their enhanced metabolic stability achieved by replacing a labile C-N bond with a C-C bond to nucleobases. Herein, a direct metallaphotoredox deoxygenative arylation to access heteroaryl C-nucleosides is described. Leveraging high-throughput experimentation, a pyridine-carboxamidine nickel precatalyst was identified as being optimal for cross-coupling with various heteroaryl bromides. Additionally, a range of modified ribose and glucose derivatives were evaluated, demonstrating the broad applicability of this transformation for the rapid synthesis of structurally diverse C-nucleosides.
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