Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans‐Metal‐Trapping

This study establishes a new trans‐metal‐trapping (TMT) procedure based on a mixture of LiTMP (the base) and tris(trimethylsilylmethyl)gallium [Ga(CH(2)SiMe(3))(3), GaR(3)] (the trap) that, operating in a tandem manner, is effective for the regioselective deprotonation of sensitive diazines in hydro...

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Detalles Bibliográficos
Autores principales: Uzelac, Marina, Kennedy, Alan R., Hevia, Eva, Mulvey, Robert E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5113679/
https://www.ncbi.nlm.nih.gov/pubmed/27647741
http://dx.doi.org/10.1002/anie.201607284
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author Uzelac, Marina
Kennedy, Alan R.
Hevia, Eva
Mulvey, Robert E.
author_facet Uzelac, Marina
Kennedy, Alan R.
Hevia, Eva
Mulvey, Robert E.
author_sort Uzelac, Marina
collection PubMed
description This study establishes a new trans‐metal‐trapping (TMT) procedure based on a mixture of LiTMP (the base) and tris(trimethylsilylmethyl)gallium [Ga(CH(2)SiMe(3))(3), GaR(3)] (the trap) that, operating in a tandem manner, is effective for the regioselective deprotonation of sensitive diazines in hydrocarbon solution, as illustrated through reactions of pyrazine, pyridazine, and pyrimidine, as well as through the N‐S heterocycle benzothiazole. The metallo‐activated complexes of all of these compounds were isolated and structurally defined.
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spelling pubmed-51136792016-12-02 Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans‐Metal‐Trapping Uzelac, Marina Kennedy, Alan R. Hevia, Eva Mulvey, Robert E. Angew Chem Int Ed Engl Communications This study establishes a new trans‐metal‐trapping (TMT) procedure based on a mixture of LiTMP (the base) and tris(trimethylsilylmethyl)gallium [Ga(CH(2)SiMe(3))(3), GaR(3)] (the trap) that, operating in a tandem manner, is effective for the regioselective deprotonation of sensitive diazines in hydrocarbon solution, as illustrated through reactions of pyrazine, pyridazine, and pyrimidine, as well as through the N‐S heterocycle benzothiazole. The metallo‐activated complexes of all of these compounds were isolated and structurally defined. John Wiley and Sons Inc. 2016-10-06 2016-10-10 /pmc/articles/PMC5113679/ /pubmed/27647741 http://dx.doi.org/10.1002/anie.201607284 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (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 Communications
Uzelac, Marina
Kennedy, Alan R.
Hevia, Eva
Mulvey, Robert E.
Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans‐Metal‐Trapping
title Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans‐Metal‐Trapping
title_full Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans‐Metal‐Trapping
title_fullStr Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans‐Metal‐Trapping
title_full_unstemmed Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans‐Metal‐Trapping
title_short Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans‐Metal‐Trapping
title_sort transforming litmp lithiation of challenging diazines through gallium alkyl trans‐metal‐trapping
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5113679/
https://www.ncbi.nlm.nih.gov/pubmed/27647741
http://dx.doi.org/10.1002/anie.201607284
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