Synthesis of Non‐Classical Arylated C‐Saccharides through Nickel/Photoredox Dual Catalysis

The development of synthetic tools to introduce saccharide derivatives into functionally complex molecules is of great interest, particularly in the field of drug discovery. Herein, we report a new route toward highly functionalized, arylated saccharides, which involves nickel‐catalyzed cross‐coupli...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-05, Vol.57 (22), p.6614-6618
Main Authors: Dumoulin, Audrey, Matsui, Jennifer K., Gutiérrez‐Bonet, Álvaro, Molander, Gary A.
Format: Article
Language:English
Subjects:
1,4-dihydropyridines
Aromatic compounds
Bromides
Carbohydrates
Catalysis
Chemical synthesis
Coupling (molecular)
Drug discovery
Glycosides
glycosylation
homogeneous catalysis
Molecular chains
Molecular Structure
Nickel
Nickel - chemistry
Oxidation-Reduction
Photochemical Processes
photoredox chemistry
Saccharides
Sugars - chemical synthesis
Sugars - chemistry
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Summary:The development of synthetic tools to introduce saccharide derivatives into functionally complex molecules is of great interest, particularly in the field of drug discovery. Herein, we report a new route toward highly functionalized, arylated saccharides, which involves nickel‐catalyzed cross‐coupling of photoredox‐generated saccharyl radicals with a range of aryl‐ and heteroaryl bromides, triggered by an organic photocatalyst. In contrast to existing methods, the mild reaction conditions achieve arylation of saccharide motifs while leaving the anomeric carbon available, thus providing access to a class of arylated glycosides that has been underexplored until now. To demonstrate the potential of this strategy in late‐stage functionalization, a variety of structurally complex molecules incorporating saccharide moieties were synthesized. Running mild: A new route toward highly functionalized, arylated saccharides through nickel‐catalyzed cross‐coupling of photoredox‐generated saccharyl radicals with a range of aryl‐ and heteroaryl bromides, triggered by an organic photocatalyst, was developed. In contrast to existing methods, the mild reaction conditions achieve arylation of saccharide motifs while leaving the anomeric carbon atom available, thereby providing access to underexplored arylated glycosides.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201802282