Palladium-Catalyzed Selective α-Alkenylation of Pyridylmethyl Ethers with Vinyl Bromides

Org Lett. 2016 May 20;18(10):2371-4. doi: 10.1021/acs.orglett.6b00815. Epub 2016 May 10.

Abstract

An efficient palladium-catalyzed α-alkenylation of pyridylmethyl ethers with vinyl bromides is presented. A Pd/NIXANTPHOS-based catalyst system enables a mild and chemoselective coupling between a variety of pyridylmethyl ethers and vinyl bromides in good to excellent yields. Under the mild conditions, β,γ-unsaturated products are obtained without isomerization or Heck byproducts observed.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic
  • Ethers / chemical synthesis*
  • Ethers / chemistry
  • Hydrogen Bonding
  • Palladium / chemistry*
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Vinyl Compounds / chemistry*

Substances

  • Ethers
  • Pyridines
  • Vinyl Compounds
  • Palladium
  • vinyl bromide