Selective Palladium-Catalyzed Domino Heck/Buchwald–Hartwig Arylations of N-Glycosylcinnamamides: An Efficient Route to 4-Aryl-N-glycosylquinolin-2-ones

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Abstract

An efficient and selective domino Heck/Buchwald–Hartwig arylations of readily available N-glycosylcinnamamides with aryl iodides have been established. Using palladium(II) acetate as a catalyst, potassium acetate as the base and tetrabutylamonium bromide as an additive in dioxane, the protocol proved to be general, and a variety of 4-aryl-N-glycosylquinolin-2-ones has been prepared in good yields with exclusive α- or β-selectivity. (Figure presented.).

Original languageEnglish
Pages (from-to)1320-1330
Number of pages11
JournalAdvanced Synthesis and Catalysis
Volume359
Issue number8
DOIs
Publication statusPublished - 17 Apr 2017
Externally publishedYes

Keywords

  • 4-aryl-N-glycosylquinolin-2-ones
  • Heck/Buchwald–Hartwig reactions
  • N-glycosylcinnamamides
  • palladium catalysis

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