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Magnesium‐Mediated Benzothiazole Activation: A Room‐Temperature Cascade of CH Deprotonation, CC 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.