Synthesis of functionalized benzo[b]thiophenes by the intramolecular copper-catalyzed carbomagnesiation of alkynyl(aryl)thioethers

Article abstract of DOI:10.1002/anie.201106734

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.