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Structural Motifs of Alkali Metal Superbases in Non‐coordinating Solvents

Lochmann–Schlosser superbases (LSB) are a standard reagent in synthetic chemistry to achieve an exchange of a proton on an organic framework with an alkali metal cation, which in turn can be replaced by a wide range of electrophilic groups. In standard examples, the deprotonating reagent consists of...

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Autor principal: Klett, Jan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7839563/
https://www.ncbi.nlm.nih.gov/pubmed/33165981
http://dx.doi.org/10.1002/chem.202002812
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author Klett, Jan
author_facet Klett, Jan
author_sort Klett, Jan
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description Lochmann–Schlosser superbases (LSB) are a standard reagent in synthetic chemistry to achieve an exchange of a proton on an organic framework with an alkali metal cation, which in turn can be replaced by a wide range of electrophilic groups. In standard examples, the deprotonating reagent consists of an equimolar mixture of n‐butyllithium and potassium t‐butoxide. However, the nature of the reactive species could not be pinned down either for this composition or for similar mixtures with comparable high reactivity. Despite the poor solubility and the fierce reactivity, some insights into this mixture were achieved by some indirect results, comparison with chemically related systems, or skillful deductions. Recent results, mainly based on new soluble compounds, delivered structural evidence. These new insights lead to advanced and more detailed conclusions about the interplay of the involved components.
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spelling pubmed-78395632021-02-01 Structural Motifs of Alkali Metal Superbases in Non‐coordinating Solvents Klett, Jan Chemistry Minireviews Lochmann–Schlosser superbases (LSB) are a standard reagent in synthetic chemistry to achieve an exchange of a proton on an organic framework with an alkali metal cation, which in turn can be replaced by a wide range of electrophilic groups. In standard examples, the deprotonating reagent consists of an equimolar mixture of n‐butyllithium and potassium t‐butoxide. However, the nature of the reactive species could not be pinned down either for this composition or for similar mixtures with comparable high reactivity. Despite the poor solubility and the fierce reactivity, some insights into this mixture were achieved by some indirect results, comparison with chemically related systems, or skillful deductions. Recent results, mainly based on new soluble compounds, delivered structural evidence. These new insights lead to advanced and more detailed conclusions about the interplay of the involved components. John Wiley and Sons Inc. 2020-11-09 2021-01-13 /pmc/articles/PMC7839563/ /pubmed/33165981 http://dx.doi.org/10.1002/chem.202002812 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/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Minireviews
Klett, Jan
Structural Motifs of Alkali Metal Superbases in Non‐coordinating Solvents
title Structural Motifs of Alkali Metal Superbases in Non‐coordinating Solvents
title_full Structural Motifs of Alkali Metal Superbases in Non‐coordinating Solvents
title_fullStr Structural Motifs of Alkali Metal Superbases in Non‐coordinating Solvents
title_full_unstemmed Structural Motifs of Alkali Metal Superbases in Non‐coordinating Solvents
title_short Structural Motifs of Alkali Metal Superbases in Non‐coordinating Solvents
title_sort structural motifs of alkali metal superbases in non‐coordinating solvents
topic Minireviews
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7839563/
https://www.ncbi.nlm.nih.gov/pubmed/33165981
http://dx.doi.org/10.1002/chem.202002812
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