Issue 30, 2022

Azidoborolate anions and azidoborole adducts: isolable forms of an unstable borole azide

Abstract

Boroles are well known to undergo ring expansion reactions with organic azides to yield 1,2-azaborinines. A synthon featuring both azide and borole moieties within the same molecule, 1-azido-2,3,4,5-tetraphenylborole, was found to be much less stable than the related, previously-reported azidoborafluorene and decomposed to intractable mixtures well below room temperature. It could, however, be trapped at −75 °C through the formation of Lewis base adducts, even in the form of the “azide-stabilized azidoborole” complex anion diazidoborolate. DFT calculations provide a rationale for the low stability of the azidoborole under study.

Graphical abstract: Azidoborolate anions and azidoborole adducts: isolable forms of an unstable borole azide

Supplementary files

Article information

Article type
Communication
Submitted
27 1 2022
Accepted
14 3 2022
First published
16 3 2022

Chem. Commun., 2022,58, 4735-4738

Azidoborolate anions and azidoborole adducts: isolable forms of an unstable borole azide

F. Lindl, F. Fantuzzi, L. Mailänder, C. Hörl, G. Bélanger-Chabot and H. Braunschweig, Chem. Commun., 2022, 58, 4735 DOI: 10.1039/D2CC00543C

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