Highly electron-deficient and air-stable conjugated thienylboranes

Xiaodong Yin, Jiawei Chen, Roger A. Lalancette, Todd B. Marder, Frieder Jäkle

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109 Scopus citations


Introduced herein is a series of conjugated thienylboranes, which are inert to air and moisture, and even resist acids and strong bases. X-ray analyses reveal a coplanar arrangement of the thiophene rings, an arrangement which facilitates p-π conjugation through the boron atoms despite the presence of highly bulky 2,4,6-tri-tert-butylphenyl (Mes*) or 2,4,6- tris(trifluoromethyl)phenyl (FMes) groups. Short B⋯F contacts, which lead to a pseudotrigonal bipyramidal geometry in the FMes species, have been further studied by DFT and AIM analysis. In contrast to the Mes* groups, the highly electron-withdrawing FMes groups do not diminish the Lewis acidity of boron toward F- anions. These compounds can be lithiated or iodinated under electrophilic conditions without decomposition, thus offering a promising route to larger conjugated structures with electron-acceptor character.

Original languageEnglish (US)
Pages (from-to)9761-9765
Number of pages5
JournalAngewandte Chemie - International Edition
Issue number37
StatePublished - Sep 8 2014

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)


  • Lewis acids
  • boron
  • conjugation
  • fluoride
  • heterocycles


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