Transforming LiTMP lithiation of challenging diazines via gallium alkyl trans-metal-trapping

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Abstract

This study establishes a new trans-metal-trapping (TMT) protocol based on a mixture of LiTMP (the base) and tris(trimethylsilylmethyl)gallium [Ga(CH2SiMe3)3, GaR3] (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 which have been isolated and structurally defined.
LanguageEnglish
Pages13147-13150
Number of pages4
JournalAngewandte Chemie International Edition
Volume55
DOIs
Publication statusPublished - 20 Sep 2016

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Pyrazines
Deprotonation
Gallium
pyrazines
pyrimidines
Hydrocarbons
gallium
hydrocarbons
Metals
trapping
traps
metals
pyrimidine
benzothiazole
pyridazine

Keywords

  • trans-metal-trapping
  • TMT
  • sensitive diazines
  • LiTMP lithiation

Cite this

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title = "Transforming LiTMP lithiation of challenging diazines via gallium alkyl trans-metal-trapping",
abstract = "This study establishes a new trans-metal-trapping (TMT) protocol based on a mixture of LiTMP (the base) and tris(trimethylsilylmethyl)gallium [Ga(CH2SiMe3)3, GaR3] (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 which have been isolated and structurally defined.",
keywords = "trans-metal-trapping, TMT, sensitive diazines, LiTMP lithiation",
author = "Marina Uzelac and Kennedy, {Alan R.} and Eva Hevia and Mulvey, {Robert E.}",
note = "This is the peer reviewed version of the following article: Transforming LiTMP lithiation of challenging diazines via gallium alkyl trans-metal-trapping. / Uzelac, Marina; Kennedy, Alan R.; Hevia, Eva; Mulvey, Robert E. In: Angewandte Chemie International Edition, 06.09.2016., which has been published in final form at http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.",
year = "2016",
month = "9",
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doi = "10.1002/anie.201607284",
language = "English",
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AU - Uzelac, Marina

AU - Kennedy, Alan R.

AU - Hevia, Eva

AU - Mulvey, Robert E.

N1 - This is the peer reviewed version of the following article: Transforming LiTMP lithiation of challenging diazines via gallium alkyl trans-metal-trapping. / Uzelac, Marina; Kennedy, Alan R.; Hevia, Eva; Mulvey, Robert E. In: Angewandte Chemie International Edition, 06.09.2016., which has been published in final form at http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

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N2 - This study establishes a new trans-metal-trapping (TMT) protocol based on a mixture of LiTMP (the base) and tris(trimethylsilylmethyl)gallium [Ga(CH2SiMe3)3, GaR3] (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 which have been isolated and structurally defined.

AB - This study establishes a new trans-metal-trapping (TMT) protocol based on a mixture of LiTMP (the base) and tris(trimethylsilylmethyl)gallium [Ga(CH2SiMe3)3, GaR3] (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 which have been isolated and structurally defined.

KW - trans-metal-trapping

KW - TMT

KW - sensitive diazines

KW - LiTMP lithiation

UR - http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773

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EP - 13150

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