Synthesis of sterically hindered polychlorinated biphenyl derivatives

S. N. Joshi, S. M. Vyas, M. W. Duffel, S. Parkin, H. J. Lehmler

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

A series of sterically hindered (methoxylated) polychlorinated biphenyl derivatives were synthesized using the Suzuki and the Ullmann coupling reactions. The Suzuki coupling with Pd(dba)2-dicyclohexylphosphino-2,6- dimethoxybiphenyl (DPDB) gave better yields (65-98%) compared to the classic Ullmann coupling reaction (20-38%). Despite the reactive catalyst system, no significant coupling with aromatic chlorine substituents was observed. Crystal structure analysis of four PCB derivatives revealed solid state dihedral angles ranging from 69.7 to 81.0, which indicates that these highly ortho-substituted PCB derivatives have some conformational flexibility.

Original languageEnglish
Pages (from-to)1045-1054
Number of pages10
JournalSynthesis
Issue number7
DOIs
StatePublished - 2011

Keywords

  • Suzuki cross-coupling
  • Ullmann cross-coupling
  • biaryls
  • dihedral angle
  • palladium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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