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Halide-Coupled Double Electron Transfer with Electron-Rich Diboranes.

Authors
  • Filbeck, Erik1
  • Cremer, Sebastian1
  • Jansen, Moritz C F1
  • Kaifer, Elisabeth1
  • Himmel, Hans-Jörg1
  • 1 Inorganic Chemistry, Ruprecht-Karls University of Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany. , (Germany)
Type
Published Article
Journal
Chemistry - A European Journal
Publisher
Wiley (John Wiley & Sons)
Publication Date
Dec 22, 2023
Volume
29
Issue
72
Identifiers
DOI: 10.1002/chem.202302911
PMID: 37728170
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

The ditriflato-diborane B2 (μ-hpp)2 (OTf)2 (hpp=1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidinate) acts as a stable surrogate of the elusive dication [B2 (hpp)2 ]2+ , being both electrophilic (vacant boron p orbitals) and nucleophilic (filled B-B bond orbital). This combination of seemingly contrasting behaviors could be used to develop a metallomimetic diborane chemistry, with Lewis σ-basic and π-acidic substrates being bound and reduced at the diborane. Here, we report on a novel reaction type within this general theme, in which double electron transfer from the diboron unit to the boron-bound organic substrate is coupled with halide transfer in the other direction. Novel diborylated dienamines are synthesized in this way. The scope of this unprecedented reaction motif and the reaction pathways are elucidated. © 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

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