Issue 34, 2023

Boroles from alumoles: accessing boroles with alkyl-substituted backbones via transtrielation

Abstract

The alumole Cp3tAlC4Et4 (Cp3t = 1,2,4-tris(tert-butyl)cyclopentadienyl) is reported to be capable of transferring its butadiene moiety to aryl(dihalo)boranes to generate boroles through aluminum–boron exchange. The products feature a rare alkyl-substituted backbone, which, as shown in other examples, often leads to dimerization due to insufficient steric protection of the antiaromatic borole ring. Sterically crowded aryl groups bound to the boron atom are shown to prevent dimerization, allowing access to the first monomeric derivatives of this type. Results from UV-vis spectroscopy, electrochemistry, and DFT calculations reveal that the alkyl substituents cause remarkable modifications in the optical and electronic properties of the boroles compared to their perarylated counterparts.

Graphical abstract: Boroles from alumoles: accessing boroles with alkyl-substituted backbones via transtrielation

Supplementary files

Article information

Article type
Edge Article
Submitted
26 5 2023
Accepted
14 7 2023
First published
19 7 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 9010-9015

Boroles from alumoles: accessing boroles with alkyl-substituted backbones via transtrielation

J. L. Bohlen, L. Endres, R. Drescher, K. Radacki, M. Dietz, I. Krummenacher and H. Braunschweig, Chem. Sci., 2023, 14, 9010 DOI: 10.1039/D3SC02668J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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