Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Functionalization of Organotrifluoroborates via Cu-Catalyzed C-N Coupling Reaction

  • Lee, Jung-Hyun (Advanced Organic Synthesis Laboratory, Department of Chemistry and Nano Science, Ewha Womans University) ;
  • Kim, Heejin (MarineChemomics Laboratory, Natural Medicine Center, Korea Institute of Science and Technology) ;
  • Kim, Taejung (MarineChemomics Laboratory, Natural Medicine Center, Korea Institute of Science and Technology) ;
  • Song, Jung Ho (MarineChemomics Laboratory, Natural Medicine Center, Korea Institute of Science and Technology) ;
  • Kim, Won-Suk (Advanced Organic Synthesis Laboratory, Department of Chemistry and Nano Science, Ewha Womans University) ;
  • Ham, Jungyeob (MarineChemomics Laboratory, Natural Medicine Center, Korea Institute of Science and Technology)
  • Received : 2012.09.11
  • Accepted : 2012.09.12
  • Published : 2013.01.20
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Abstract

Potassium N-heterobiaryltrifluoroborates were successfully prepared via a selective Cu-catalyzed C-N coupling reaction. The $BF_3K$ moiety was well tolerated under the reaction conditions involving CuI and dimethyl-ethylenediamine (DMEDA) in the presence of DMSO. The Pd-catalyzed Suzuki-Miyaura cross couplings of potassium N-heterobiaryltrifluoroborates with bromoarenes were studied to prepare the N-heterotriaryl compounds. Moreover, homocoupling, iodination, and hydroxylation of potassium N-heterobiaryltrifluoroborates provided the corresponding products in high yields.

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