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 Jan 2022
Accepted
14 Mar 2022
First published
16 Mar 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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