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Synthesis of Functionalized Benzo[ b ]thiophenes by the Intramolecular Copper‐Catalyzed Carbomagnesiation of Alkynyl(aryl)thioethers
Author(s) -
Kunz Thomas,
Knochel Paul
Publication year - 2012
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.201106734
Subject(s) - benzothiophene , chemistry , intramolecular force , aryl , electrophile , catalysis , medicinal chemistry , copper , organic chemistry , halide , combinatorial chemistry , thiophene , alkyl
Highly functional: A copper(I)‐catalyzed intramolecular carbomagnesiation under mild conditions transforms readily available alkynyl(aryl)thioethers into magnesiated benzothiophenes. Subsequent reaction with various electrophiles (acid chlorides, allyl bromides, aryl halides) provides polyfunctional benzo[ b ]thiophenes (see scheme). Further modification of the cyclization products affords highly diversified benzothiophene derivatives and new heterocyclic scaffolds.