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Org Lett. 2004 Oct 28;6(22):3981-3.

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

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  • 1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.


[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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