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Palladium-catalyzed cross-coupling of pyrrole anions with aryl chlorides, bromides, and iodides.

Authors
  • Rieth, Ryan D
  • Mankad, Neal P
  • Calimano, Elisa
  • Sadighi, Joseph P
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Oct 28, 2004
Volume
6
Issue
22
Pages
3981–3983
Identifiers
PMID: 15496079
Source
Medline
License
Unknown

Abstract

[reaction: see text] A general method for the conversion of pyrrole anions to 2-arylpyrroles has been developed. Using a palladium precatalyst and sterically demanding 2-(dialkylphosphino)biphenyl ligands, (pyrrolyl)zinc chloride may be cross-coupled with a wide range of aryl halides, including aryl chlorides and aryl bromides, at low catalyst loadings and under mild conditions. A high degree of steric hindrance is tolerated. Certain ring-substituted pyrrole anions have also been arylated with aryl bromide substrates.

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