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.
- cascade reactions
- mixed-metal chemistry
Blair, V. L., Clegg, W., Kennedy, A. R., Livingstone, Z., Russo, L., & Hevia, E. (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), 9857-9860. https://doi.org/10.1002/anie.201103275