Issue 60, 2024

Aromaticity transfer in an annulated 1,4,2-diazaborole: facile access to Cs symmetric 1,4,2,5-diazadiborinines

Abstract

A tricyclic annulated 1,4,2-diazaborole is readily accessed via reaction of a bidentate pyridyl-carbene ligand with MesBBr2 followed by reduction. Dearomatization of the flanking rings is shown to increase reactivity of this heterocycle in the form of a B-centred alkylation with MeI. Its reaction with hydrido-, fluoro-, and chloro-boranes reveal an unprecedented ring expansion reaction to form a diverse family of B2C2N2 heterocycles, reduction of which allows facile access to the first examples of Cs symmetric 1,4,2,5-diazadiborinines. DFT calculations have shed light on the electronic structures of the reduced species and provide insight into mechanistic aspects of the observed ring-expansion.

Graphical abstract: Aromaticity transfer in an annulated 1,4,2-diazaborole: facile access to Cs symmetric 1,4,2,5-diazadiborinines

Supplementary files

Article information

Article type
Communication
Submitted
20 Cax 2024
Accepted
30 Qas 2024
First published
02 Qad 2024

Chem. Commun., 2024,60, 7705-7708

Aromaticity transfer in an annulated 1,4,2-diazaborole: facile access to Cs symmetric 1,4,2,5-diazadiborinines

V. Pattathil and C. Pranckevicius, Chem. Commun., 2024, 60, 7705 DOI: 10.1039/D4CC02414A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements