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A Domino Annulation Reaction under Willgerodt−Kindler Conditions

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posted on 20.06.2008, 00:00 by Daniel Kadzimirsz, Daniel Kramer, Lertnarong Sripanom, Iris M. Oppel, Pawel Rodziewicz, Nikos L. Doltsinis, Gerald Dyker
Butanone side chains at arenes and hetarenes, efficiently introduced by a Heck-type reaction, are transformed to annulated thieno[3,2-b]thiophenes in a domino redox process under Willgerodt−Kindler conditions. A nucleophilic aromatic substitution with an intermediary thioenolate is a reasonable key step of this process.