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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 4: 1551 - 1562

DOI: https://doi.org/10.6023/cjoc202010027

ARTICLES

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

  • Yuren Sun ,
  • Jiandong Liu ,
  • Quan Lin ,
  • Ken Yao ,
  • Weiqi Tong ,
  • Qun Qian
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  • a School of Materials Science and Engineering, Center for Supramolecular Chemistry and Catalysis, Shanghai 200444
    b College of Sciences, Shanghai University, Shanghai 200444
* Corresponding author. E-mail:

Received date: 2020-10-20

  Revised date: 2020-11-12

  Online published: 2020-12-05

Supported by

National Natural Science Foundation of China(21871173)

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Abstract

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 α-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%~5% yields. This method can be scaled up on a gram scale by lowering the loading of nickel catalyst to 2 mol%.

Key words： nickel-catalysis; reductive coupling; α-selective preparation; C-aryl glycoside; gram scale

Cite this article

Yuren Sun , Jiandong Liu , Quan Lin , Ken Yao , Weiqi Tong , Qun Qian . Facile Preparation of Aryl C-Glycosides by Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Aryl Halides[J]. Chinese Journal of Organic Chemistry, 2021 , 41(4) : 1551 -1562 . DOI: 10.6023/cjoc202010027

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