Synthesis of polychlorinated biphenyls and their metabolites with a modified Suzuki-coupling

Izabela Kania-Korwel, Sean Parkin, Larry W. Robertson, Hans Joachim Lehmler

Research output: Contribution to journalArticlepeer-review

24 Scopus citations


A modified procedure for the synthesis of polychlorinated biphenyls (PCBs) utilizing the Suzuki-coupling, a palladium-catalyzed cross-coupling reaction, is described. The coupling of (chlorinated) benzene boronic acids with bromochlorobenzenes, using Pd(dppf)2Cl2 (dppf=1,1 -bis(diphenylphosphino)ferrocene) as the catalyst and aqueous sodium carbonate as the base, gave the desired PCB congeners in moderate to good yields. Eleven PCB congeners, including environmentally important PCB congeners and metabolites, were synthesized using this modified procedure. This new catalyst Pd(dppf)2Cl2 offers the advantage of being less air-sensitive and has a longer shelf life compared to Pd(PPh4) 4. Three new (di-)methoxylated PCB congeners were synthesized using the same procedure by either coupling a chlorinated benzene boronic acid with a bromo (di-)methoxybenzene or by coupling a (di-)methoxy benzene boronic acid with a chlorinated bromobenzene. The dimethoxylated PCB congeners were readily converted into the respective dihydroxylated PCB derivatives using boron tribromide in dichloromethane. This approach offers the advantage of high selectivity and moderate to good yields compared to conventional methods such as the Cadogan reaction and allows the use of less toxic starting materials.

Original languageEnglish
Pages (from-to)735-744
Number of pages10
Issue number8
StatePublished - Aug 2004

Bibliographical note

Funding Information:
The authors would like to thank Drs. Bummer (University of Kentucky, Lexington, USA) and Flanagan (University of Iowa, Iowa City, USA) for access to the DSC instruments. The project was supported by grant number P42 ES 07380 from the National Institute of Environmental Health Sciences, NIH. Its contents are solely the responsibility of the authors and do not necessarily represent the official views of the NIEHS or EPA. I.K.K. gratefully acknowledges the support of a Fulbright Junior Research Grant and a Kosciuszko Foundation Grant.


  • Cross-coupling
  • Methoxylated PCB
  • PCB
  • Palladium
  • Synthesis

ASJC Scopus subject areas

  • Environmental Engineering
  • Environmental Chemistry
  • General Chemistry
  • Pollution
  • Health, Toxicology and Mutagenesis


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