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

Research output: Contribution to journalArticle

  • 2 Citations

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.
LanguageEnglish
Number of pages4
JournalChemical Communications
Early online date1 Sep 2017
DOIs
StateE-pub ahead of print - 1 Sep 2017

Fingerprint

Thymidine Monophosphate
Pyridines
Pyrazines
Triazoles
Clamping devices
Amides
Pyridine
Magnesium
Anions
Negative ions
Ligands
Molecules

Keywords

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

Cite this

@article{4a3ff23b2c2641f48bb7dbdfadf805a8,
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",
author = "Laia Davin and Ross McLellan and Alberto Hern{\'a}n-G{\'o}mez and Bill Clegg and Kennedy, {A R} and Iain Stepek and Maria Mertens and Eva Hevia",
year = "2017",
month = "9",
day = "1",
doi = "10.1039/C6CC09675A",
language = "English",
journal = "Chemical Communications",
issn = "1359-7345",

}

Regioselective magnesiation of N-heterocyclic molecules: securing insecure cyclic anions by a β-diketiminate-magnesium clamp. / Davin, Laia; McLellan, Ross; Hernán-Gómez, Alberto; Clegg, Bill; Kennedy, A R; Stepek, Iain; Mertens, Maria; Hevia, Eva.

In: Chemical Communications, 01.09.2017.

Research output: Contribution to journalArticle

TY - JOUR

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

JO - Chemical Communications

T2 - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

ER -