Dialkylboryl-Substituted Cyclic Disilenes Synthesized by Desilylation-Borylation of Trimethylsilyl-Substituted Disilenes

Kaho Tanaka, Naohiko Akasaka, Tomoyuki Kosai, Shunya Honda, Yuya Ushijima, Shintaro Ishida, Takeaki Iwamoto

Research output: Contribution to journalArticlepeer-review

Abstract

π-Electron systems of silicon have attracted attention because of their narrow HOMO-LUMO gap and high reactivity, but the structural diversity remains limited. Herein, new dialkylboryl-substituted disilenes were synthesized by the selective desilylation-borylation of the corresponding trimethylsilyl-substituted disilenes. The dialkylboryl-substituted disilenes were fully characterized by a combination of NMR spectroscopy, MS spectrometry, single-crystal X-ray diffraction analysis, and theoretical calculations. The longest-wavelength absorption bands of boryldisilenes were bathochromically shifted compared to the corresponding silyl-substituted disilenes, indicating a substantial conjugation between π(Si=Si) and vacant 2p(B) orbitals. In the presence of 4-(dimethylamino)pyridine (DMAP), the dialkylboryl groups in the boryl-substituted disilenes were easily converted to trimethylsilyl groups, suggesting the dialkylboryl-substituted disilenes in the presence of a base serve as the surrogates of disilenyl anions (disilenides).

Original languageEnglish
JournalMolecules (Basel, Switzerland)
Volume26
Issue number6
DOIs
Publication statusPublished - 2021 Mar 15

Keywords

  • borylation
  • desilylation
  • disilene
  • disilenide
  • trimethylsilyl
  • UV-vis spectrum
  • X-ray analysis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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