Magnesium-mediated benzothiazole activation : a room temperature cascade of C-H deprotonation, C-C coupling, ring-opening and nucleophilic addition reactions

Blair, Victoria L. and Clegg, William and Kennedy, Alan R. and Livingstone, Zoe and Russo, Luca and Hevia, Eva (2011) Magnesium-mediated benzothiazole activation : a room temperature cascade of C-H deprotonation, C-C coupling, ring-opening and nucleophilic addition reactions. Angewandte Chemie, 50 (42). pp. 9857-9860. ISSN 0044-8249 (https://doi.org/10.1002/anie.201103275)

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Abstract

Ligand domin(o)ated: In contrast to the straightforward deprotonation of benzothiazole using Grignard reagents, treatment of benzothiazole with 1 leads to a novel type of activation. The initial magnesiation initiates an unstoppable domino reaction of CC coupling, ring opening, nucleophilic addition, and deprotonation to give 2. THF=tetrahydrofuran.

ORCID iDs

Blair, Victoria L., Clegg, William, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Livingstone, Zoe, Russo, Luca and Hevia, Eva ORCID logoORCID: https://orcid.org/0000-0002-3998-7506;
  • Item type:Article
    ID code:34747
    Dates:
    Date
    Event
    10 October 2011
    Published
    Keywords:cascade reactions, heterocylces, magnesium, metalation, mixed-metal chemistry, Chemistry, Medicine(all)
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:20 Oct 2011 19:28
    Last modified:24 Nov 2022 14:40
    URI:https://strathprints.strath.ac.uk/id/eprint/34747
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