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Nickel-catalyzed reductive coupling of glucosyl halides with aryl/vinyl halides enabling β-selective preparation of C-aryl/vinyl glucosides

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Abstract

This work describes stereoselective preparation of β-C-aryl/vinyl glucosides via mild Ni-catalyzed reductive arylation and vinylation of C1-glucosyl halides with aryl and vinyl halides. A broad range of aryl halides and vinyl halides were employed to yield C-aryl/vinyl glucosides in 42%–93% yields. Good to excellent β-selectivities were obtained for C-glucosides by using tridentate ligand.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21871173, 21572140, 21372151).

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Authors and Affiliations

  1. School of Materials Science and Engineering, Center for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, Shanghai, 200444, China

    Jiandong Liu, Chuanhu Lei & Hegui Gong

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  1. Jiandong Liu
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  2. Chuanhu Lei
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  3. Hegui Gong
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Corresponding authors

Correspondence to Chuanhu Lei or Hegui Gong.

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Liu, J., Lei, C. & Gong, H. Nickel-catalyzed reductive coupling of glucosyl halides with aryl/vinyl halides enabling β-selective preparation of C-aryl/vinyl glucosides. Sci. China Chem. 62, 1492–1496 (2019). https://doi.org/10.1007/s11426-019-9501-4

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