Cobaloxime-Catalyzed Radical C-Allyl Glycoside Assembly

A direct allylic C-H glycosylation reaction is described, which involves the synergistic merger of photoredox-halogen atom transfer (XAT)/cobalt catalysis. This reaction enhances the application of Giese addition in the synthesis of <i>C</i>-alkyl glycosides by Co<sup>II</sup> capturing the alkyl radical intermediate/β-hydrogen abstraction to deliver highly valuable allyl glycosylation products. Moreover, the compatibility with the late-stage functionalization of pharmaceutical molecules and the potential for scalable production underscore the practical utility of this protocol in synthetic applications.

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Publication Details

Journal
Organic Letters
Published
2026-01-29
DOI
https://doi.org/10.1021/acs.orglett.5c05219
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Cobaloxime-Catalyzed Radical C-Allyl Glycoside Assembly

Yong-Min LIANG, Rui-Qiang Jiao, Hongyin Gao, Jia-Le Sun et al.
Organic Letters
Radical Photochemical Reactions
article

Cobaloxime-Catalyzed Radical C-Allyl Glycoside Assembly

Yong-Min LIANG, Rui-Qiang Jiao, Hongyin Gao, Jia-Le Sun, Wen-Xin Cui
article en

Abstract

A direct allylic C-H glycosylation reaction is described, which involves the synergistic merger of photoredox-halogen atom transfer (XAT)/cobalt catalysis. This reaction enhances the application of Giese addition in the synthesis of <i>C</i>-alkyl glycosides by Co<sup>II</sup> capturing the alkyl radical intermediate/β-hydrogen abstraction to deliver highly valuable allyl glycosylation products. Moreover, the compatibility with the late-stage functionalization of pharmaceutical molecules and the potential for scalable production underscore the practical utility of this protocol in synthetic applications.

Organic LettersVol. 28(6)
Ningxia University (CN), Green Chemistry (PL), State Key Laboratory of Applied Organic Chemistry, Lanzhou University (CN)
Openalex Percentile: Top 73%
Radical Photochemical Reactions
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