Magnesium‐Mediated Benzothiazole Activation: A Room‐Temperature Cascade of CH Deprotonation, CC Coupling, Ring‐Opening, and Nucleophilic Addition Reactions | Zendy

Blair Victoria L. | Zendy; Clegg William | Zendy; Kennedy Alan R. | Zendy; Livingstone Zoe | Zendy; Russo Luca | Zendy; Hevia Eva | Zendy

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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

Author(s) -

Blair Victoria L.,

Clegg William,

Kennedy Alan R.,

Livingstone Zoe,

Russo Luca,

Hevia Eva

Publication year - 2011

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201103275

Subject(s) - deprotonation , benzothiazole , nucleophile , chemistry , ring (chemistry) , tetrahydrofuran , reagent , domino , magnesium , grignard reagent , coupling (piping) , stereochemistry , medicinal chemistry , organic chemistry , materials science , catalysis , ion , solvent , metallurgy

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.

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