Alkene insertion reactivity of a o-carboranyl-substituted 9-borafluorene

Tobias Bischof; Xueying Guo; Ivo Krummenacher; Lukas Beßler; Zhenyang Lin; Maik Finze; Holger Braunschweig

doi:10.1039/D2SC02750J

Alkene insertion reactivity of a o-carboranyl-substituted 9-borafluorene†

Tobias Bischof,‡^ab Xueying Guo,

‡^c Ivo Krummenacher,^ab Lukas Beßler,^ab Zhenyang Lin,

*^c Maik Finze

*^ab and Holger Braunschweig

*^ab

Author affiliations

* Corresponding authors

^a Institute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
E-mail: maik.finze@uni-wuerzburg.de, h.braunschweig@uni-wuerzburg.de

^b Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg, Germany

^c Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, P. R. China
E-mail: chzlin@ust.hk

Abstract

The synthesis of 9-borafluorene with an electron-withdrawing o-carboranyl substituent and its reactions with a series of alkenes are described. The o-carboranyl substituent is bonded via one of the cluster carbon atoms to the boron atom of the 9-borafluorene moiety. In all cases, the reactions afford partly saturated analogs of borepins (i.e. 6,7-dihydroborepins) by unprecedented alkene insertion into the endocyclic B–C bond of the borole ring. Comparative studies with 9-bromo-9-borafluorene illustrate the superior insertion reactivity of the carboranyl-substituted derivative. A suite of experimental and computational techniques disclose the unique properties of the 9-borafluorene and provide insight into how the 9-carboranyl substituent affects its chemical reactivity.

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DOI: https://doi.org/10.1039/D2SC02750J
Article type: Edge Article
Submitted: 17 May 2022
Accepted: 01 Jun 2022
First published: 02 Jun 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2022,13, 7492-7497

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Alkene insertion reactivity of a o-carboranyl-substituted 9-borafluorene

T. Bischof, X. Guo, I. Krummenacher, L. Beßler, Z. Lin, M. Finze and H. Braunschweig, Chem. Sci., 2022, 13, 7492 DOI: 10.1039/D2SC02750J

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Chemical Science

Alkene insertion reactivity of a o-carboranyl-substituted 9-borafluorene†

Abstract

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Alkene insertion reactivity of a o-carboranyl-substituted 9-borafluorene

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