State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
J Org Chem. 2022 Jul 1;87(13):8811-8818. doi: 10.1021/acs.joc.2c00815. Epub 2022 Jun 13.
Metal-catalyzed CH glycosylation reactions with glycosyl chloride donors have emerged as a useful strategy for the synthesis of -glycosides. Previously, palladium and nickel complexes were reported to catalyze CH glycosylation reactions using amide-linked bidentate auxiliaries. Herein, a ruthenium-catalyzed ortho CH glycosylation reaction of arenes with various glycosyl chloride donors using a monodentate pyridine directing group is developed. Preliminary mechanistic studies indicated that two-electron oxidative addition and reductive elimination of ruthenocycle intermediate led to the glycosylation products.
金属催化的 CH 糖苷化反应与糖基氯供体一起，已成为合成β-糖苷的有效策略。此前，已有报道称钯和镍配合物使用酰胺连接的双齿辅助配体催化 CH 糖苷化反应。在此，开发了一种使用单齿吡啶导向基团的钌催化芳基与各种糖基氯供体的邻位 CH 糖苷化反应。初步的机理研究表明，钌环中间体的两电子氧化加成和还原消除导致了糖苷化产物的生成。
