4.8 Article

GeCl2•Dioxane-AgBF4 Catalyzed Activation of Glycosyl Fluorides for Glycosylation

Journal

ORGANIC LETTERS
Volume 24, Issue 20, Pages 3626-3630

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01146

Keywords

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Funding

  1. Youth Innovation Promotion Association of CAS [2021251]
  2. National Key Research & Development Program of China [2018YFA0507602]
  3. National Natural Science Foundation of China [22031011, 21621002, 21871290]
  4. Key Research Program of Frontier Sciences of the Chinese Academy of Sciences [ZDBS-LY-SLH030]
  5. Shanghai Municipal Science and Technology Major Project

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A catalytic glycosyl fluoride activation system using the GeCl2·dioxane-AgBF4 combination was developed, involving reversible activation of C-F bond and reversible chloride ion transfer. This system is easy to operate, proceeds at room temperature, and has a broad scope of substrates.
A catalytic glycosyl fluoride activation system using the GeCl2 center dot dioxane-AgBF4 combination was developed, which involves a reversible activation of the anomeric C-F bond by a [Ge(II)-Cl](+) cation and a reversible chloride ion transfer between Ge(II) and glycosyl cations. This catalytic glycosylation system is easy to operate, proceeds at room temperature, and offers a broad scope of substrates.

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