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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

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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.