4.5 Article

Synthesis of C6-Substituted Purine Nucleoside Analogues via Late-Stage Photoredox/Nickel Dual Catalytic Cross-Coupling

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ACS MEDICINAL CHEMISTRY LETTERS
卷 12, 期 4, 页码 662-666

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AMER CHEMICAL SOC
DOI: 10.1021/acsmedchemlett.0c00673

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Purine nucleosides; photoredox; cross-electrophile; late-stage diversification

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This study presents a strategy for functionalizing purine nucleosides through photoredox and nickel-catalyzed sp(2)-sp(3) cross-coupling, allowing for coupling of unprotected nucleosides with readily available alkyl bromides, providing opportunities for their application in parallel medicinal chemistry.
Nucleoside analogues have been and continue to be extremely important compounds in drug discovery. Despite the significant effort dedicated to their synthesis, medicinal chemistry campaigns around these structures are often hampered by synthetic challenges. We describe a strategy for the functionalization of purine nucleosides via photoredox and nickel-catalyzed sp(2)-sp(3) cross-coupling. The conditions described herein allow for coupling of unprotected nucleosides with readily available alkyl bromides, providing opportunities for their application to parallel medicinal chemistry.

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