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

Marina Uzelac; Alan R. Kennedy; Eva Hevia; Robert E. Mulvey

doi:10.1002/anie.201607284

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

Marina Uzelac, Alan R. Kennedy, Eva Hevia, Robert E. Mulvey

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

37 Citations (Scopus)

97 Downloads (Pure)

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.

Original language	English
Pages (from-to)	13147-13150
Number of pages	4
Journal	Angewandte Chemie International Edition
Volume	55
DOIs	https://doi.org/10.1002/anie.201607284
Publication status	Published - 20 Sept 2016

Keywords

trans-metal-trapping
TMT
sensitive diazines
LiTMP lithiation

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10.1002/anie.201607284Licence: CC BY 4.0

Uzelac-etal-AC-2016-Transforming-LiTMP-lithiation-of-challenging-diazines-via-gallium-alkyl-trans-metal-trappingFinal published version, 1.09 MBLicence: CC BY 4.0

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 = sep,

day = "20",

doi = "10.1002/anie.201607284",

language = "English",

volume = "55",

pages = "13147--13150",

journal = "Angewandte Chemie International Edition",

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TY - JOUR

T1 - Transforming LiTMP lithiation of challenging diazines via gallium alkyl trans-metal-trapping

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.

PY - 2016/9/20

Y1 - 2016/9/20

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

U2 - 10.1002/anie.201607284

DO - 10.1002/anie.201607284

M3 - Article

SN - 1433-7851

VL - 55

SP - 13147

EP - 13150

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

ER -

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

Abstract

Keywords

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Robert Mulvey

Towards a Paradigm Shift in the Principles and Practice of Polar Organometallic Chemistry

MIXMETAPPS: Tailoring Mixed-Metal Chemistry For Frontier Synthetic And Catalytic Applications (ERC Starting Grant)

Data for: "Transforming LiTMP lithiation of challenging diazines via gallium alkyl trans-metal-trapping"

x-ray diffractometer

Cite this

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Profiles

Robert Mulvey

Projects

Towards a Paradigm Shift in the Principles and Practice of Polar Organometallic Chemistry

MIXMETAPPS: Tailoring Mixed-Metal Chemistry For Frontier Synthetic And Catalytic Applications (ERC Starting Grant)

Datasets

Data for: "Transforming LiTMP lithiation of challenging diazines via gallium alkyl trans-metal-trapping"

Equipment

x-ray diffractometer

Cite this