Stereoselective Decarboxylative <i>C</i> -Alkenylation of Anomeric Glycosyl Carboxylic Acids through Cobalt–Photoredox Dual Catalysis

Alkenyl C-glycosides hold significant value across diverse applications, yet their synthetic methodologies remain underdeveloped. Particularly, the simultaneous precise control of the anomeric selectivity and the geometry of the double bond poses a formidable synthetic challenge. Herein, we report that the use of a cost-effective and nontoxic cobaloxime complex enables a dual anomeric and Z/E-stereoselective photocatalytic synthesis of alkenyl C-glycosides from simple and stable glycosyl carboxylic acids and terminal alkenes.

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Publication Details

Journal
ACS Catalysis
Published
2025-11-04
DOI
https://doi.org/10.1021/acscatal.5c06029
Citations
1
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.94
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article

Stereoselective Decarboxylative C -Alkenylation of Anomeric Glycosyl Carboxylic Acids through Cobalt–Photoredox Dual Catalysis

Wei Zhao, Mingxiang Zhu, Samir Messaoudi, Fang Zhang et al.
1 citations
ACS Catalysis
Radical Photochemical Reactions
0.94
article

Stereoselective Decarboxylative C -Alkenylation of Anomeric Glycosyl Carboxylic Acids through Cobalt–Photoredox Dual Catalysis

Wei Zhao, Mingxiang Zhu, Samir Messaoudi, Fang Zhang, Huiying Chen, Jinyang Hai
article en
1 citations

Abstract

Alkenyl C-glycosides hold significant value across diverse applications, yet their synthetic methodologies remain underdeveloped. Particularly, the simultaneous precise control of the anomeric selectivity and the geometry of the double bond poses a formidable synthetic challenge. Herein, we report that the use of a cost-effective and nontoxic cobaloxime complex enables a dual anomeric and Z/E-stereoselective photocatalytic synthesis of alkenyl C-glycosides from simple and stable glycosyl carboxylic acids and terminal alkenes.

ACS CatalysisVol. 15(22)
Ministry of Education of the People's Republic of China (CN), École Polytechnique (FR), Shanghai Normal University (CN), Laboratoire de Synthèse Organique (FR), Institut Polytechnique de Paris (FR)
Openalex Percentile: Top 20%
Radical Photochemical Reactions
0.94
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