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Updated: Jan 31, 2026
09:10
Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
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Cobaloxime-Catalyzed Radical C-Allyl Glycoside Assembly
Rui-Qiang Jiao1, Wen-Xin Cui1, Jia-Le Sun1
1School of Chemistry and Chemical Engineering, State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, Ningxia University, Yinchuan 750021, China.
Organic Letters
|January 29, 2026
Summary
A novel direct allylic C-H glycosylation reaction was developed using photoredox and cobalt catalysis. This method efficiently synthesizes valuable C-alkyl glycosides, applicable to late-stage functionalization and scalable production.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Allylic C-H functionalization is crucial for synthesizing complex organic molecules.
- Developing efficient methods for C-glycoside synthesis remains a significant challenge in organic chemistry.
Purpose of the Study:
- To develop a direct allylic C-H glycosylation reaction.
- To enhance the Giese addition for C-alkyl glycoside synthesis.
- To provide a scalable and versatile method for late-stage functionalization.
Main Methods:
- Synergistic photoredox and cobalt catalysis.
- Halogen atom transfer (XAT) mechanism.
- Radical intermediate capture and beta-hydrogen abstraction.
Main Results:
- Successful direct allylic C-H glycosylation.
- Efficient synthesis of C-alkyl glycosides.
- Demonstrated compatibility with late-stage functionalization of pharmaceutical molecules.
Conclusions:
- The developed protocol offers a powerful new route to allyl glycosylation products.
- The method exhibits practical utility for scalable synthesis and pharmaceutical applications.
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