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Updated: Jun 4, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Stereoselective Synthesis of (Hetero)aryl C-Nucleosides via Mild Decarboxylative Reductive Cross-Electrophile
1Process Research & Development, MRL, Merck & Co., Inc., West Point, Pennsylvania 19486, United States.
Abstract:
C-nucleosides represent an important yet synthetically challenging class of targets in drug discovery. Herein, we report a mild synthesis of (hetero)aryl C-nucleosides via decarboxylative reductive cross-electrophile coupling of ribosyl N-hydroxyphthalimide esters with widely abundant and structurally diverse aryl bromides. This modular approach operates under homogeneous, room temperature conditions, exhibiting broad substrate scope and functional group compatibility across a variety of furanosides and pyranosides. Notably, we demonstrated this methodology in a Parallel Medicinal Chemistry (PMC) workflow to deliver a library of diverse (hetero)aryl C-nucleosides.
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