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

  • Wei Zhao
  • , Jinyang Hai
  • , Huiying Chen
  • , Samir Messaoudi
  • , Mingxiang Zhu
  • , Fang Zhang

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)19127-19134
Number of pages8
JournalACS Catalysis
Volume15
DOIs
Publication statusPublished - 1 Jan 2025
Externally publishedYes

Keywords

  • C-glycosides
  • Cobaloxime catalysis
  • Decarboxylative alkenylation
  • Dual stereocontrol
  • Photoredox catalysis

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