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
12 ذو القعدة 1445
Accepted
24 ذو الحجة 1445
First published
26 ذو الحجة 1445

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

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