The 9H‐9‐Borafluorene Dianion: A Surrogate for Elusive Diarylboryl Anion Nucleophiles

Double reduction of the THF adduct of 9H‐9‐borafluorene (1⋅THF) with excess alkali metal affords the dianion salts M(2)[1] in essentially quantitative yields (M=Li–K). Even though the added charge is stabilized through π delocalization, [1](2−) acts as a formal boron nucleophile toward organoboron (...

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Autores principales: Gilmer, Jannik, Budy, Hendrik, Kaese, Thomas, Bolte, Michael, Lerner, Hans‐Wolfram, Wagner, Matthias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7155136/
https://www.ncbi.nlm.nih.gov/pubmed/31834978
http://dx.doi.org/10.1002/anie.201914219
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author Gilmer, Jannik
Budy, Hendrik
Kaese, Thomas
Bolte, Michael
Lerner, Hans‐Wolfram
Wagner, Matthias
author_facet Gilmer, Jannik
Budy, Hendrik
Kaese, Thomas
Bolte, Michael
Lerner, Hans‐Wolfram
Wagner, Matthias
author_sort Gilmer, Jannik
collection PubMed
description Double reduction of the THF adduct of 9H‐9‐borafluorene (1⋅THF) with excess alkali metal affords the dianion salts M(2)[1] in essentially quantitative yields (M=Li–K). Even though the added charge is stabilized through π delocalization, [1](2−) acts as a formal boron nucleophile toward organoboron (1⋅THF) and tetrel halide electrophiles (MeCl, Et(3)SiCl, Me(3)SnCl) to form B−B/C/Si/Sn bonds. The substrate dependence of open‐shell versus closed‐shell pathways has been investigated.
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spelling pubmed-71551362020-04-15 The 9H‐9‐Borafluorene Dianion: A Surrogate for Elusive Diarylboryl Anion Nucleophiles Gilmer, Jannik Budy, Hendrik Kaese, Thomas Bolte, Michael Lerner, Hans‐Wolfram Wagner, Matthias Angew Chem Int Ed Engl Communications Double reduction of the THF adduct of 9H‐9‐borafluorene (1⋅THF) with excess alkali metal affords the dianion salts M(2)[1] in essentially quantitative yields (M=Li–K). Even though the added charge is stabilized through π delocalization, [1](2−) acts as a formal boron nucleophile toward organoboron (1⋅THF) and tetrel halide electrophiles (MeCl, Et(3)SiCl, Me(3)SnCl) to form B−B/C/Si/Sn bonds. The substrate dependence of open‐shell versus closed‐shell pathways has been investigated. John Wiley and Sons Inc. 2020-01-22 2020-03-27 /pmc/articles/PMC7155136/ /pubmed/31834978 http://dx.doi.org/10.1002/anie.201914219 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Gilmer, Jannik
Budy, Hendrik
Kaese, Thomas
Bolte, Michael
Lerner, Hans‐Wolfram
Wagner, Matthias
The 9H‐9‐Borafluorene Dianion: A Surrogate for Elusive Diarylboryl Anion Nucleophiles
title The 9H‐9‐Borafluorene Dianion: A Surrogate for Elusive Diarylboryl Anion Nucleophiles
title_full The 9H‐9‐Borafluorene Dianion: A Surrogate for Elusive Diarylboryl Anion Nucleophiles
title_fullStr The 9H‐9‐Borafluorene Dianion: A Surrogate for Elusive Diarylboryl Anion Nucleophiles
title_full_unstemmed The 9H‐9‐Borafluorene Dianion: A Surrogate for Elusive Diarylboryl Anion Nucleophiles
title_short The 9H‐9‐Borafluorene Dianion: A Surrogate for Elusive Diarylboryl Anion Nucleophiles
title_sort 9h‐9‐borafluorene dianion: a surrogate for elusive diarylboryl anion nucleophiles
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7155136/
https://www.ncbi.nlm.nih.gov/pubmed/31834978
http://dx.doi.org/10.1002/anie.201914219
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