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Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperature†‡
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2018-06-28 00:00:00 , DOI: 10.1039/c8ob01393d
Adesh Kumar Singh 1, 2, 3, 4 , Jeyakumar Kandasamy 1, 2, 3, 4
Affiliation  

A stereocontrolled synthesis of aryl-C-glycosides was achieved using glycals and aryldiazonium salts in the presence of palladium acetate. A wide range of glycals including D-glucal, D-galactal, L-rhamnal, D-xylal and D-ribal underwent C-arylation at the anomeric carbon in the presence of different aryldiazonium tetrafluoroborates and gave synthetically useful 2,3-deoxy-3-keto-α-aryl-C-glycosides in good to excellent yields. Broad substrate scope, simple operation and room temperature reactions make this protocol very attractive in organic synthesis.

中文翻译:

钯在室温下使用糖和戊二烯鎓盐催化钯催化立体合成C-芳基糖苷

芳基的立体控制合成Ç使用烯糖和芳基重氮盐在乙酸钯的存在下达到-glycosides。宽范围的烯糖,包括d -glucal,d -galactal,大号-rhamnal,d -xylal和d -ribal后行Ç -arylation在不同的芳基重氮四氟硼酸盐的存在下异头碳,并给合成有用2,3-脱氧3-酮- α -芳基- C ^ -glycosides以良好至优异的产量。广泛的底物范围,简单的操作和室温反应使该方案在有机合成中非常有吸引力。
更新日期:2018-06-28
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