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

Davin, Laia and McLellan, Ross and Hernán-Gómez, Alberto and Clegg, Bill and Kennedy, A R and Stepek, Iain and Mertens, Maria and Hevia, Eva (2017) Regioselective magnesiation of N-heterocyclic molecules: securing insecure cyclic anions by a β-diketiminate-magnesium clamp. Chemical Communications. ISSN 1359-7345

[img]
Preview
 Text (Davin-etal-CC2017-regioselective-magnesiation-of-N-heterocyclic-molecules)
Davin_etal_CC2017_regioselective_magnesiation_of_N_heterocyclic_molecules.pdf
Accepted Author Manuscript
Download (899kB)| Preview

    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.

    Creators(s): Davin, Laia ORCID logoORCID: https://orcid.org/0000-0002-7927-4930, McLellan, Ross ORCID logoORCID: https://orcid.org/0000-0001-9700-0258, Hernán-Gómez, Alberto ORCID logoORCID: https://orcid.org/0000-0001-8150-7249, Clegg, Bill, Kennedy, A R ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Stepek, Iain, Mertens, Maria and Hevia, Eva ORCID logoORCID: https://orcid.org/0000-0002-3998-7506;
    Item type:Article
    ID code:59343
    Keywords:magnesium metallating manifold, regioselective strategy , magnesiation, N-heterocyclic molecules, synthesis, chrage density, deprotonative metalation, Chemistry, Chemistry(all)
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:10 Jan 2017 10:32
    Last modified:18 Sep 2020 04:42
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/59343
    Export data:
    CORE (COnnecting REpositories)