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Weakly stabilized primary borenium cations and their dicationic dimers.

Aleksandrs Prokofjevs1, Jeff W Kampf, Andrey Solovyev

  • 1Department of Chemistry, University of Michigan , Ann Arbor, Michigan 48109, United States.

Journal of the American Chemical Society
|October 4, 2013
PubMed
Summary

Researchers generated observable borenium cations from hydride bridged salts. Depending on the Lewis base used, either primary borenium cations or highly reactive dicationic dimers were formed, revealing new insights into boron chemistry.

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Area of Science:

  • Organoboron Chemistry
  • Carbocation Chemistry
  • Supramolecular Chemistry

Background:

  • Boron cations are typically highly reactive and transient species.
  • The stabilization of boron cations is crucial for understanding their reactivity and synthetic utility.
  • Hydride bridged boron compounds offer a potential route to generating and isolating novel boron cations.

Purpose of the Study:

  • To investigate the generation of borenium cations via hydride abstraction from monocationic hydride bridged salts.
  • To explore the influence of different Lewis bases (L) on the stability and structure of the resulting boron cations.
  • To characterize the observable primary borenium cation and the dicationic dimers formed.

Main Methods:

  • Synthesis of monocationic hydride bridged salts [H(H2B-L)2]+ with various Lewis bases (L).
  • Hydride abstraction reactions using a suitable reagent.
  • Spectroscopic characterization (e.g., NMR) of the generated boron species.
  • Crystallographic analysis for structural determination.

Main Results:

  • An observable primary borenium cation was successfully generated when L = iPr2NEt.
  • With alternative Lewis bases such as L = Me3N, Me2NPr, and N-heterocyclic carbenes, highly reactive dicationic dimers were formed instead.
  • The choice of Lewis base dictates the outcome of the hydride abstraction, leading to distinct boron cation species.

Conclusions:

  • The study demonstrates the feasibility of generating observable borenium cations through controlled hydride abstraction.
  • The nature of the Lewis base is a critical factor in determining the stability and aggregation state of the boron cations.
  • This work provides a foundation for the synthesis and study of novel boron-containing reactive intermediates.