Highly electron-deficient and air-stable conjugated thienylboranes

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

Research output: Contribution to journalArticle

69 Citations (Scopus)

Abstract

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
Volume53
Issue number37
DOIs
StatePublished - Sep 8 2014

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Boron
Thiophenes
Electrons
Thiophene
Air
Acidity
Discrete Fourier transforms
Anions
Moisture
Negative ions
Decomposition
X rays
Atoms
Acids
Geometry

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

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Highly electron-deficient and air-stable conjugated thienylboranes. / Yin, Xiaodong; Chen, Jiawei; Lalancette, Roger; Marder, Todd B.; Jaekle, Frieder.

In: Angewandte Chemie - International Edition, Vol. 53, No. 37, 08.09.2014, p. 9761-9765.

Research output: Contribution to journalArticle

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