Triptycene Boronates, Boranes, and Boron Ate-Complexes: Toward Sterically Hindered Triarylboranes and Trifluoroborates

Mathieu Gama; Xavier Antognini Silva; Thu Hong Doan; Arnaud Osi; Aurélien Chardon; Nikolay Tumanov; Johan Wouters; Guillaume Berionni

doi:10.1002/ejoc.202001672

Triptycene Boronates, Boranes, and Boron Ate-Complexes: Toward Sterically Hindered Triarylboranes and Trifluoroborates

Mathieu Gama, Xavier Antognini Silva, Thu Hong Doan, Arnaud Osi, Aurélien Chardon, Nikolay Tumanov, Johan Wouters, Guillaume Berionni

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

We developed two synthetic strategies towards triptycene-derived bulky boranes, boronates, and boron ate-complexes. Starting from borylated or brominated anthracenes and using a Br/Li exchange and [4+2] cycloaddition reaction with in-situ generated benzyne, we produced a series of triptycene boronates and borates with various boron substituents in positions 1 and 9, such as BPin, Bneo, BF₃K and B(Mes)₂. Single-crystal X-ray diffraction analysis and UV-Vis/photoluminescence measurements provided quantitative information on the effect of the triptycene scaffold on the photophysical and electronic properties of the obtained compounds.

langue originale	Anglais
Pages (de - à)	1440-1445
Nombre de pages	6
journal	European Journal of Organic Chemistry
Volume	2021
Numéro de publication	9
Les DOIs	https://doi.org/10.1002/ejoc.202001672
Etat de la publication	Publié - 5 mars 2021

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ejoc.202001672 Triptycene Boronates, Boranes, and Boron Ate-Complexes
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title = "Triptycene Boronates, Boranes, and Boron Ate-Complexes: Toward Sterically Hindered Triarylboranes and Trifluoroborates",

abstract = "We developed two synthetic strategies towards triptycene-derived bulky boranes, boronates, and boron ate-complexes. Starting from borylated or brominated anthracenes and using a Br/Li exchange and [4+2] cycloaddition reaction with in-situ generated benzyne, we produced a series of triptycene boronates and borates with various boron substituents in positions 1 and 9, such as BPin, Bneo, BF3K and B(Mes)2. Single-crystal X-ray diffraction analysis and UV-Vis/photoluminescence measurements provided quantitative information on the effect of the triptycene scaffold on the photophysical and electronic properties of the obtained compounds.",

keywords = "Lewis acids, Organoboron chemistry, Sterically hindered compounds, Triptycenes",

author = "Mathieu Gama and {Antognini Silva}, Xavier and Doan, {Thu Hong} and Arnaud Osi and Aur{\'e}lien Chardon and Nikolay Tumanov and Johan Wouters and Guillaume Berionni",

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doi = "10.1002/ejoc.202001672",

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Triptycene Boronates, Boranes, and Boron Ate-Complexes: Toward Sterically Hindered Triarylboranes and Trifluoroborates. / Gama, Mathieu; Antognini Silva, Xavier; Doan, Thu Hong et al.
Dans: European Journal of Organic Chemistry, Vol 2021, Numéro 9, 05.03.2021, p. 1440-1445.

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

TY - JOUR

T1 - Triptycene Boronates, Boranes, and Boron Ate-Complexes

T2 - Toward Sterically Hindered Triarylboranes and Trifluoroborates

AU - Gama, Mathieu

AU - Antognini Silva, Xavier

AU - Doan, Thu Hong

AU - Osi, Arnaud

AU - Chardon, Aurélien

AU - Tumanov, Nikolay

AU - Wouters, Johan

AU - Berionni, Guillaume

PY - 2021/3/5

Y1 - 2021/3/5

N2 - We developed two synthetic strategies towards triptycene-derived bulky boranes, boronates, and boron ate-complexes. Starting from borylated or brominated anthracenes and using a Br/Li exchange and [4+2] cycloaddition reaction with in-situ generated benzyne, we produced a series of triptycene boronates and borates with various boron substituents in positions 1 and 9, such as BPin, Bneo, BF3K and B(Mes)2. Single-crystal X-ray diffraction analysis and UV-Vis/photoluminescence measurements provided quantitative information on the effect of the triptycene scaffold on the photophysical and electronic properties of the obtained compounds.

AB - We developed two synthetic strategies towards triptycene-derived bulky boranes, boronates, and boron ate-complexes. Starting from borylated or brominated anthracenes and using a Br/Li exchange and [4+2] cycloaddition reaction with in-situ generated benzyne, we produced a series of triptycene boronates and borates with various boron substituents in positions 1 and 9, such as BPin, Bneo, BF3K and B(Mes)2. Single-crystal X-ray diffraction analysis and UV-Vis/photoluminescence measurements provided quantitative information on the effect of the triptycene scaffold on the photophysical and electronic properties of the obtained compounds.

KW - Lewis acids

KW - Organoboron chemistry

KW - Sterically hindered compounds

KW - Triptycenes

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DO - 10.1002/ejoc.202001672

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SN - 1434-193X

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JO - European Journal of Organic Chemistry

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Triptycene Boronates, Boranes, and Boron Ate-Complexes: Toward Sterically Hindered Triarylboranes and Trifluoroborates

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