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Ruthenium-Catalyzed Pyridine-Directed Aryl C–H Glycosylation with Glycosyl Chlorides
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-06-13 , DOI: 10.1021/acs.joc.2c00815 Shaokun Cai 1 , Qikai Sun 1 , Quanquan Wang 1 , Gang He 1 , Gong Chen 1
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2022-06-13 , DOI: 10.1021/acs.joc.2c00815 Shaokun Cai 1 , Qikai Sun 1 , Quanquan Wang 1 , Gang He 1 , Gong Chen 1
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Metal-catalyzed C–H glycosylation reactions with glycosyl chloride donors have emerged as a useful strategy for the synthesis of C-glycosides. Previously, palladium and nickel complexes were reported to catalyze C–H glycosylation reactions using amide-linked bidentate auxiliaries. Herein, a ruthenium-catalyzed ortho C–H 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.
中文翻译：
钌催化吡啶定向芳基 C-H 糖基化与糖基氯化物
与糖基氯供体的金属催化 C - H 糖基化反应已成为合成C-糖苷的有用策略。以前，据报道钯和镍配合物使用酰胺连接的双齿助剂催化 C - H 糖基化反应。在此，开发了使用单齿吡啶导向基团的钌催化芳烃与各种糖基氯供体的邻 C - H 糖基化反应。初步机理研究表明，钌环中间体的双电子氧化加成和还原消除导致糖基化产物。
更新日期：2022-06-13
中文翻译：
钌催化吡啶定向芳基 C-H 糖基化与糖基氯化物
与糖基氯供体的金属催化 C - H 糖基化反应已成为合成C-糖苷的有用策略。以前，据报道钯和镍配合物使用酰胺连接的双齿助剂催化 C - H 糖基化反应。在此，开发了使用单齿吡啶导向基团的钌催化芳烃与各种糖基氯供体的邻 C - H 糖基化反应。初步机理研究表明，钌环中间体的双电子氧化加成和还原消除导致糖基化产物。
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