Copper-Catalyzed Stereoselective Borylation and Palladium-Catalyzed Stereospecific Cross-Coupling to Give Aryl C-Glycosides

Kazuki Kurahayashi, Kengo Hanaya, Takeshi Sugai, Go Hirai, Shuhei Higashibayashi

Research output: Contribution to journalArticlepeer-review

Abstract

Metabolically stable C-glycosides are an essential family of compounds in bioactive natural products, therapeutic agents, and biological probes. For their application, development of synthetic methods by connecting glycosides and aglycons with strict stereocontrol at the anomeric carbon, as well as with high functional-group compatibility and environmental compatibility is a pivotal issue. Although Suzuki–Miyaura-type C(sp3)−C(sp2) cross-coupling using glycosyl boronates is a potential candidate for the construction of C-glycosides, neither the cross-coupling itself nor the facile synthesis of the coupling precursor, glycosyl boronates, have been achieved to date. Herein, it was succeeded to develop a copper-catalyzed stereoselective one-step borylation of glycosyl bromides to glycosyl boronates and palladium-catalyzed stereospecific cross-coupling of β-glycosyl borates with aryl bromides to give aryl β-C-glycosides, in which the β-configuration of the anomeric carbon of the glycosyl trifluoroborates is stereoretentively transferred to that of the resulting aryl C-glycosides.

Original languageEnglish
Article numbere202203376
JournalChemistry - A European Journal
Volume29
Issue number6
DOIs
Publication statusPublished - 2023 Jan 27

Keywords

  • aryl C-glycosides
  • borylation
  • cross-coupling
  • glycosyl borates
  • glycosyl halides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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