Regioselective magnesiation of N-heterocyclic molecules: securing insecure cyclic anions by a β-diketiminate-magnesium clamp

Laia Davin; Ross McLellan; Alberto Hernán-Gómez; Bill Clegg; A R Kennedy; Iain Stepek; Maria Mertens; Eva Hevia

doi:10.1039/C6CC09675A

Regioselective magnesiation of N-heterocyclic molecules: securing insecure cyclic anions by a β-diketiminate-magnesium clamp

Laia Davin, Ross McLellan, Alberto Hernán-Gómez, Bill Clegg, A R Kennedy, Iain Stepek, Maria Mertens, Eva Hevia

Pure And Applied Chemistry

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

21 Citations (Scopus)

18 Downloads (Pure)

Abstract

Using a specially designed magnesium metallating manifold, combining kinetically activated TMP amide base with a sterically amplified β-diketiminate ligand, this study has established a new regioselective strategy for magnesiation of challenging N-heterocyclic molecules. The broad scope of the approach is illustrated through reactions of pyrazine, triazoles and substituted pyridines through isolation and structural elucidation of their magnesiated intermediates.

Original language	English
Number of pages	4
Journal	Chemical Communications
Early online date	1 Sept 2017
DOIs	https://doi.org/10.1039/C6CC09675A
Publication status	E-pub ahead of print - 1 Sept 2017

Keywords

magnesium metallating manifold
regioselective strategy
magnesiation
N-heterocyclic molecules
synthesis
chrage density
deprotonative metalation

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10.1039/C6CC09675A

Davin-etal-CC2017-regioselective-magnesiation-of-N-heterocyclic-moleculesAccepted author manuscript, 879 KB

Cite this

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title = "Regioselective magnesiation of N-heterocyclic molecules: securing insecure cyclic anions by a β-diketiminate-magnesium clamp",

abstract = "Using a specially designed magnesium metallating manifold, combining kinetically activated TMP amide base with a sterically amplified β-diketiminate ligand, this study has established a new regioselective strategy for magnesiation of challenging N-heterocyclic molecules. The broad scope of the approach is illustrated through reactions of pyrazine, triazoles and substituted pyridines through isolation and structural elucidation of their magnesiated intermediates.",

keywords = "magnesium metallating manifold, regioselective strategy , magnesiation, N-heterocyclic molecules, synthesis, chrage density, deprotonative metalation",

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language = "English",

journal = "Chemical Communications",

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T1 - Regioselective magnesiation of N-heterocyclic molecules: securing insecure cyclic anions by a β-diketiminate-magnesium clamp

AU - Davin, Laia

AU - McLellan, Ross

AU - Hernán-Gómez, Alberto

AU - Clegg, Bill

AU - Kennedy, A R

AU - Stepek, Iain

AU - Mertens, Maria

AU - Hevia, Eva

PY - 2017/9/1

Y1 - 2017/9/1

N2 - Using a specially designed magnesium metallating manifold, combining kinetically activated TMP amide base with a sterically amplified β-diketiminate ligand, this study has established a new regioselective strategy for magnesiation of challenging N-heterocyclic molecules. The broad scope of the approach is illustrated through reactions of pyrazine, triazoles and substituted pyridines through isolation and structural elucidation of their magnesiated intermediates.

AB - Using a specially designed magnesium metallating manifold, combining kinetically activated TMP amide base with a sterically amplified β-diketiminate ligand, this study has established a new regioselective strategy for magnesiation of challenging N-heterocyclic molecules. The broad scope of the approach is illustrated through reactions of pyrazine, triazoles and substituted pyridines through isolation and structural elucidation of their magnesiated intermediates.

KW - magnesium metallating manifold

KW - regioselective strategy

KW - magnesiation

KW - N-heterocyclic molecules

KW - synthesis

KW - chrage density

KW - deprotonative metalation

UR - http://pubs.rsc.org/en/journals/journalissues/cc#!recentarticles&adv

U2 - 10.1039/C6CC09675A

DO - 10.1039/C6CC09675A

M3 - Article

SN - 1359-7345

JO - Chemical Communications

JF - Chemical Communications

ER -

Regioselective magnesiation of N-heterocyclic molecules: securing insecure cyclic anions by a β-diketiminate-magnesium clamp

Abstract

Keywords

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

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Regioselective magnesiation of N-heterocyclic molecules: securing insecure cyclic anions by a β-diketiminate-magnesium clamp

Abstract

Keywords

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Other files and links

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Projects

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

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