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CC BY 4.0 · Synthesis
DOI: 10.1055/a-2738-8038
Paper
Published as part of the Special Topic Dedicated to Prof. Paul Knochel

Electrophilic C(sp2)−H Borylation of Nonactivated and Deactivated Arenes with Pyramidal Boron Lewis Superacids

Authors

  • Arnaud Osi

    1   Department of Chemistry and Namur Institute of Structured Matter (NISM), Université de Namur, Namur, Belgium (Ringgold ID: RIN54501)

  • Baptiste Neil

    1   Department of Chemistry and Namur Institute of Structured Matter (NISM), Université de Namur, Namur, Belgium (Ringgold ID: RIN54501)

  • Nicolas Niessen

    1   Department of Chemistry and Namur Institute of Structured Matter (NISM), Université de Namur, Namur, Belgium (Ringgold ID: RIN54501)

  • Aurélien Chardon

    1   Department of Chemistry and Namur Institute of Structured Matter (NISM), Université de Namur, Namur, Belgium (Ringgold ID: RIN54501)

  • Julia Volk

    1   Department of Chemistry and Namur Institute of Structured Matter (NISM), Université de Namur, Namur, Belgium (Ringgold ID: RIN54501)

  • Guillaume Berionni 

    1   Department of Chemistry and Namur Institute of Structured Matter (NISM), Université de Namur, Namur, Belgium (Ringgold ID: RIN54501)

Supported by: HORIZON EUROPE European Research Council 101044649
We acknowledge the European Research Council (ERC, B-yond, grant agreement 101044649), and the Fond National de la Recherche Scientifique (F.R.S.-FNRS) for financial support (Grant Numbers: T.0012.21 (G.B), FRIA PhD grants for A.O (1.E.097.20) and Chargé de recherche research grant for A.C (1.B.087.21F)). We thank the PC2 (UNamur) technological platforms for access to all characterization instruments.
Supported by: Université Catholique de Louvain 2.5020.11,G006.15,RW/GEQ2016,RW1610468,RW2110213,U.G011.22,U.G018.19 Supported by: Walloon Region Supported by: Fonds pour la Formation à la Recherche dans l’Industrie et dans l’Agriculture 1.B.087.21F,1.E.097.20 Supported by: Fonds De La Recherche Scientifique - FNRS T.0012.21
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Graphical Abstract

Dedication

Dedicated to Prof. Paul Knochel for his 70th birthday.

Abstract

The electrophilic C–H borylation of unactivated and deactivated, electron-poor arenes is a challenging reaction even with the most electrophilic borenium-ion species. We now report the transition-metal-free borylation of a wide range of aromatics and polyaromatics with a pyramidal boron Lewis superacid from the 9-boratriptycene family. The mechanism of formation of a highly reactive pyramidal boron Lewis superacid and the origin of the slow and continuous release of this highly reactive borylation reagent in the presence of a Lewis base are reminiscent of the reactions of latent frustrated Lewis pairs with small molecules.

Keywords

Borylations - Boron Lewis superacids - Borylating reagents - Pyramidal boranes - Boratriptycenes - C–H borylation reactions

Supplementary Material



Publication History

Received: 18 July 2025

Accepted after revision: 27 October 2025

Article published online:
19 December 2025

© 2025. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/).

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