Metal‐Free C−H Borylation of N‐Heteroarenes by Boron Trifluoride

Organoboron compounds are essential reagents in modern C−C coupling reactions. Their synthesis via catalytic C−H borylation by main group elements is emerging as a powerful tool alternative to transition metal based catalysis. Herein, a straightforward metal‐free synthesis of aryldifluoroboranes fro...

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Autores principales: Iashin, Vladimir, Berta, Dénes, Chernichenko, Konstantin, Nieger, Martin, Moslova, Karina, Pápai, Imre, Repo, Timo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7702085/
https://www.ncbi.nlm.nih.gov/pubmed/32478432
http://dx.doi.org/10.1002/chem.202001436
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author Iashin, Vladimir
Berta, Dénes
Chernichenko, Konstantin
Nieger, Martin
Moslova, Karina
Pápai, Imre
Repo, Timo
author_facet Iashin, Vladimir
Berta, Dénes
Chernichenko, Konstantin
Nieger, Martin
Moslova, Karina
Pápai, Imre
Repo, Timo
author_sort Iashin, Vladimir
collection PubMed
description Organoboron compounds are essential reagents in modern C−C coupling reactions. Their synthesis via catalytic C−H borylation by main group elements is emerging as a powerful tool alternative to transition metal based catalysis. Herein, a straightforward metal‐free synthesis of aryldifluoroboranes from BF(3) and heteroarenes is reported. The reaction is assisted by sterically hindered amines and catalytic amounts of thioureas. According to computational studies the reaction proceeds via frustrated Lewis pair (FLP) mechanism. The obtained aryldifluoroboranes are further stabilized against destructive protodeborylation by converting them to the corresponding air stable tetramethylammonium organotrifluoroborates.
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spelling pubmed-77020852020-12-14 Metal‐Free C−H Borylation of N‐Heteroarenes by Boron Trifluoride Iashin, Vladimir Berta, Dénes Chernichenko, Konstantin Nieger, Martin Moslova, Karina Pápai, Imre Repo, Timo Chemistry Full Papers Organoboron compounds are essential reagents in modern C−C coupling reactions. Their synthesis via catalytic C−H borylation by main group elements is emerging as a powerful tool alternative to transition metal based catalysis. Herein, a straightforward metal‐free synthesis of aryldifluoroboranes from BF(3) and heteroarenes is reported. The reaction is assisted by sterically hindered amines and catalytic amounts of thioureas. According to computational studies the reaction proceeds via frustrated Lewis pair (FLP) mechanism. The obtained aryldifluoroboranes are further stabilized against destructive protodeborylation by converting them to the corresponding air stable tetramethylammonium organotrifluoroborates. John Wiley and Sons Inc. 2020-09-29 2020-11-02 /pmc/articles/PMC7702085/ /pubmed/32478432 http://dx.doi.org/10.1002/chem.202001436 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Full Papers
Iashin, Vladimir
Berta, Dénes
Chernichenko, Konstantin
Nieger, Martin
Moslova, Karina
Pápai, Imre
Repo, Timo
Metal‐Free C−H Borylation of N‐Heteroarenes by Boron Trifluoride
title Metal‐Free C−H Borylation of N‐Heteroarenes by Boron Trifluoride
title_full Metal‐Free C−H Borylation of N‐Heteroarenes by Boron Trifluoride
title_fullStr Metal‐Free C−H Borylation of N‐Heteroarenes by Boron Trifluoride
title_full_unstemmed Metal‐Free C−H Borylation of N‐Heteroarenes by Boron Trifluoride
title_short Metal‐Free C−H Borylation of N‐Heteroarenes by Boron Trifluoride
title_sort metal‐free c−h borylation of n‐heteroarenes by boron trifluoride
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7702085/
https://www.ncbi.nlm.nih.gov/pubmed/32478432
http://dx.doi.org/10.1002/chem.202001436
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