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

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    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.

    ORCID iDs

    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
      Dates:
      Date
      Event
      1 September 2017
      Published
      1 September 2017
      Published Online
      5 January 2017
      Accepted
      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:09 May 2021 00:41
      Related URLs:
      URI:https://strathprints.strath.ac.uk/id/eprint/59343
    CORE (COnnecting REpositories)