Visible-Light-Mediated Metal/Base-Free Stereoselective C -Alkyl Glycosylation via EDA Complexes of Glycosyl Xanthates and NHC-Borane

作者：Yuping Liu, Qin Zhang, Zhiqiang Yu, Yuan‐Hong Tu, Zhen Wang, Qingju Zhang, Liming Wang · 发表于：Organic Letters · 年份：2025 · DOI：10.1021/acs.orglett.5c00957 · 被引用次数：8 · 研究领域：Carbohydrate Chemistry and Synthesis、Click Chemistry and Applications、Microbial Natural Products and Biosynthesis

Owing to the toxic reagent and high temperature required, the application of xanthate-based radical chemistry has been limited. To address these challenges, we report a metal- and base-free, photoinduced strategy for stereoselective C -alkyl glycosylation via electron donor–acceptor (EDA) complexes of glycosyl xanthates and N-heterocyclic carbene (NHC)-BH 3 . This method generates glycosyl radicals under mild conditions, affording compatibility with a wide range of sugars and olefins to produce C -alkyl glycosides in good to excellent yields. Mechanistic studies confirmed the formation of EDA complexes and the involvement of radical intermediates, providing insights into the reaction pathway.