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

Magnesium-mediated benzothiazole activation: a room-temperature cascade of C-H deprotonation, C-C coupling, ring-opening, and nucleophilic addition reactions.
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DOI:
10.1002/anie.201103275
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发表时间:
2011-10
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通讯作者:
V. Blair;W. Clegg;A. Kennedy;Zoe Livingstone;Luca Russo;Eva Hevia
V. Blair;W. Clegg;A. Kennedy;Zoe Livingstone;Luca Russo;Eva Hevia
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作者:
V. Blair;W. Clegg;A. Kennedy;Zoe Livingstone;Luca Russo;Eva Hevia

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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 C-C coupling, ring opening, nucleophilic addition, and deprotonation to give 2. THF=tetrahydrofuran.