One pot synthesis of diarylfurans from aryl esters and PhI(OAc)2 via palladium-associated iodonium ylides

Org Biomol Chem. 2015 Apr 14;13(14):4179-82. doi: 10.1039/c5ob00273g. Epub 2015 Mar 11.

Abstract

The example of palladium-catalyzed intermolecular cyclization for the synthesis of various diarylfurans in which one of the aromatic rings originates from the phenolic part of the starting ester and the other one from PhI(OAc)2 has been reported. The reaction is carried out through two steps: the rearrangement of palladium-associated iodonium ylides to form o-iodo diaryl ether and then palladium catalyzed intramolecular direct arylation. This reaction can tolerate a variety of functional groups and is alternative or complementary to the previous methods for the synthesis of diarylfurans.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemical synthesis*
  • Acetates / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Coordination Complexes / chemical synthesis*
  • Coordination Complexes / chemistry*
  • Esters
  • Furans / chemical synthesis*
  • Furans / chemistry*
  • Halogens / chemistry*
  • Palladium / chemistry*

Substances

  • Acetates
  • Coordination Complexes
  • Esters
  • Furans
  • Halogens
  • Palladium