Pushing the Lewis Acidity Boundaries of Boron Compounds With Non‐Planar Triarylboranes Derived from Triptycenes

Ali Ben Saida; Aurélien Chardon; Arnaud Osi; Nikolay Tumanov; Johan Wouters; Abel Idrice Adjieufack; Benoît Champagne; Guillaume Berionni

doi:10.1002/anie.201910908

Pushing the Lewis Acidity Boundaries of Boron Compounds With Non‐Planar Triarylboranes Derived from Triptycenes

Ali Ben Saida, Aurélien Chardon, Arnaud Osi, Nikolay Tumanov, Johan Wouters, Abel Idrice Adjieufack, Benoît Champagne, Guillaume Berionni

Research output: Contribution to journal › Article › peer-review

Abstract

Bending the planar trigonal boron center of triphenylborane by connecting its aryl rings with carbon or phosphorus linkers gave access to a series of 9-boratriptycene derivatives with unprecedented structures and reactivities. NMR spectroscopy and X-ray diffraction of the Lewis adducts of these non-planar boron Lewis acids with weak Lewis base revealed particularly strong covalent bond formation. The first Lewis adduct of a trivalent boron compounds with the Tf ₂N ⁻ anion illustrates the unrivaled Lewis acidity of these species. Increasing the pyramidalization of the boron center and using a cationic phosphonium linker resulted in an exceptional enhancement of Lewis acidity. Introduction of a phosphorus and a boron atom at each edge of a triptycene framework, allowed access to new bifunctional Lewis acid-base 9-phospha-10-boratriptycenes featuring promising reactivity for the activation of carbon-halogen bonds.

Original language	English
Pages (from-to)	16889-16893
Number of pages	5
Journal	Angewandte Chemie. International edition
Volume	58
Issue number	47
DOIs	https://doi.org/10.1002/anie.201910908
Publication status	Published - 18 Nov 2019

Funding

Funders	Funder number
FNRS‐FRFC	1610468, 2.5020.11, RW/GEQ2016, GEQ U.G006.15
Unité de Chimie Organique
Nepal Agricultural Research Council
Fonds de la Recherche Scientifique F.R.S.-FNRS	F.4513.18
Fonds de la Recherche Scientifique F.R.S.-FNRS
University of Namur

Keywords

boron
Lewis acids
Lewis superacid
non-planar
triarylboranes

Access to Document

10.1002/anie.201910908

https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201910908

Cite this

@article{52fe88a86a77477a877e2bb0d02fe145,

title = "Pushing the Lewis Acidity Boundaries of Boron Compounds With Non‐Planar Triarylboranes Derived from Triptycenes",

abstract = "Bending the planar trigonal boron center of triphenylborane by connecting its aryl rings with carbon or phosphorus linkers gave access to a series of 9-boratriptycene derivatives with unprecedented structures and reactivities. NMR spectroscopy and X-ray diffraction of the Lewis adducts of these non-planar boron Lewis acids with weak Lewis base revealed particularly strong covalent bond formation. The first Lewis adduct of a trivalent boron compounds with the Tf 2N − anion illustrates the unrivaled Lewis acidity of these species. Increasing the pyramidalization of the boron center and using a cationic phosphonium linker resulted in an exceptional enhancement of Lewis acidity. Introduction of a phosphorus and a boron atom at each edge of a triptycene framework, allowed access to new bifunctional Lewis acid-base 9-phospha-10-boratriptycenes featuring promising reactivity for the activation of carbon-halogen bonds. ",

keywords = "boron, Lewis acids, Lewis superacid, non-planar, triarylboranes",

author = "\{Ben Saida\}, Ali and Aur{\'e}lien Chardon and Arnaud Osi and Nikolay Tumanov and Johan Wouters and Adjieufack, \{Abel Idrice\} and Beno{\^i}t Champagne and Guillaume Berionni",

note = "Funding Information: We acknowledge the University of Namur, the Institute of Structured Matter (NISM), research college (NARC) and the Fond National de la Recherche Scientifique FNRS (grant F.4513.18 for G.B.) for funding. The quantum-chemical calculations were performed on the computing facilities of the “Consortium des {\'E}quipements de Calcul Intensif”, in particular at the High-Performance Computing technological platform (University of Namur), which is supported by the FNRS-FRFC, the Walloon Region, and the University of Namur (Conventions No. 2.5020.11, GEQ U.G006.15, 1610468, and RW/GEQ2016). We thank the PC2 technological platform for access to X-ray diffraction and NMR instruments and the Unit{\'e} de Chimie Organique team (Prof. St{\'e}phane Vincent and Prof. Steve Lanners) for useful discussions. Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2019",

month = nov,

day = "18",

doi = "10.1002/anie.201910908",

language = "English",

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AU - Ben Saida, Ali

AU - Chardon, Aurélien

AU - Osi, Arnaud

AU - Tumanov, Nikolay

AU - Wouters, Johan

AU - Adjieufack, Abel Idrice

AU - Champagne, Benoît

AU - Berionni, Guillaume

N1 - Funding Information: We acknowledge the University of Namur, the Institute of Structured Matter (NISM), research college (NARC) and the Fond National de la Recherche Scientifique FNRS (grant F.4513.18 for G.B.) for funding. The quantum-chemical calculations were performed on the computing facilities of the “Consortium des Équipements de Calcul Intensif”, in particular at the High-Performance Computing technological platform (University of Namur), which is supported by the FNRS-FRFC, the Walloon Region, and the University of Namur (Conventions No. 2.5020.11, GEQ U.G006.15, 1610468, and RW/GEQ2016). We thank the PC2 technological platform for access to X-ray diffraction and NMR instruments and the Unité de Chimie Organique team (Prof. Stéphane Vincent and Prof. Steve Lanners) for useful discussions. Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/11/18

Y1 - 2019/11/18

N2 - Bending the planar trigonal boron center of triphenylborane by connecting its aryl rings with carbon or phosphorus linkers gave access to a series of 9-boratriptycene derivatives with unprecedented structures and reactivities. NMR spectroscopy and X-ray diffraction of the Lewis adducts of these non-planar boron Lewis acids with weak Lewis base revealed particularly strong covalent bond formation. The first Lewis adduct of a trivalent boron compounds with the Tf 2N − anion illustrates the unrivaled Lewis acidity of these species. Increasing the pyramidalization of the boron center and using a cationic phosphonium linker resulted in an exceptional enhancement of Lewis acidity. Introduction of a phosphorus and a boron atom at each edge of a triptycene framework, allowed access to new bifunctional Lewis acid-base 9-phospha-10-boratriptycenes featuring promising reactivity for the activation of carbon-halogen bonds.

AB - Bending the planar trigonal boron center of triphenylborane by connecting its aryl rings with carbon or phosphorus linkers gave access to a series of 9-boratriptycene derivatives with unprecedented structures and reactivities. NMR spectroscopy and X-ray diffraction of the Lewis adducts of these non-planar boron Lewis acids with weak Lewis base revealed particularly strong covalent bond formation. The first Lewis adduct of a trivalent boron compounds with the Tf 2N − anion illustrates the unrivaled Lewis acidity of these species. Increasing the pyramidalization of the boron center and using a cationic phosphonium linker resulted in an exceptional enhancement of Lewis acidity. Introduction of a phosphorus and a boron atom at each edge of a triptycene framework, allowed access to new bifunctional Lewis acid-base 9-phospha-10-boratriptycenes featuring promising reactivity for the activation of carbon-halogen bonds.

KW - boron

KW - Lewis acids

KW - Lewis superacid

KW - non-planar

KW - triarylboranes

UR - https://www.scopus.com/pages/publications/85074495615

U2 - 10.1002/anie.201910908

DO - 10.1002/anie.201910908

M3 - Article

C2 - 31475396

SN - 1433-7851

VL - 58

SP - 16889

EP - 16893

JO - Angewandte Chemie. International edition

JF - Angewandte Chemie. International edition

IS - 47

ER -

Pushing the Lewis Acidity Boundaries of Boron Compounds With Non‐Planar Triarylboranes Derived from Triptycenes

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Pushing the Lewis Acidity Boundaries of Boron Compounds With Non‐Planar Triarylboranes Derived from Triptycenes

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