Visible-Light-Induced Pd-Catalyzed Radical Strategy for Constructing C-Vinyl Glycosides

Org Lett. 2020 Aug 21;22(16):6288-6293. doi: 10.1021/acs.orglett.0c02053. Epub 2020 Aug 4.

Abstract

A novel visible-light-induced palladium-catalyzed Heck reaction for bromine sugars and aryl olefins with high regio- and stereochemistry selectivity for the preparation of C-glycosyl styrene is described. This reaction takes place in one step at room temperature by using a simple and readily available starting material. This protocol can be scaled up to a wide range of glycosyl bromide donors and aryl olefin substrates. Mechanistic studies indicate that a radical addition pathway is involved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Glycosides / chemistry*
  • Light
  • Molecular Structure
  • Palladium / chemistry*
  • Vinyl Compounds / chemistry*

Substances

  • Alkenes
  • Glycosides
  • Vinyl Compounds
  • Palladium