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 1521-3773 (https://doi.org/10.1002/anie.201103275)

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

Kennedy, Alan R. ORCID: https://orcid.org/0000-0003-3652-6015

Hevia, Eva ORCID: https://orcid.org/0000-0002-3998-7506

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• Item metadata

  Item type:	Article
  ID code:	34747
  Dates:	Date Event 10 October 2011 Published
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	20 Oct 2011 19:28
  Last modified:	11 Nov 2024 09:54
  URI:	https://strathprints.strath.ac.uk/id/eprint/34747