Facile Preparation of Aryl C-Glycosides by Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Aryl Halides

被引：4

作者：

Sun, Yuren ^{[1
]}

Liu, Jiandong ^{[1
]}

Lin, Quan ^{[1
]}

Yao, Ken ^{[1
]}

Tong, Weiqi ^{[2
]}

Qun, Qian ^{[2
]}

机构：

[1] Ctr Supramol Chem & Catalysis, Sch Mat Sci & Engn, Shanghai 200444, Peoples R China

[2] Shanghai Univ, Coll Sci, Shanghai 200444, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 41卷 / 04期

基金：

中国国家自然科学基金;

关键词：

nickel-catalysis; reductive coupling; alpha-selective preparation; C-aryl glycoside; gram scale; EFFICIENT SYNTHESIS; ALKYL-HALIDES; INHIBITOR; ACIDS;

D O I：

10.6023/cjoc202010027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of C-aryl glycosides via mild Ni/bipyridine-catalyzed reductive arylation of C(1)-glycosyl halides with electron-deficient aryl bromides was developed. Moderate to high alpha-selectivities were achieved for C-glycosides. A broad range of aryl halides including electron-rich aryl iodides were employed to yield C-aryl glycosides in 40%similar to 5% yields. This method can be scaled up on a gram scale by lowering the loading of nickel catalyst to 2 mol%.

引用

页码：1551 / 1562

页数：12

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