Communication

Synthesis of Functionalized Benzo[b]thiophenes by the Intramolecular Copper-Catalyzed Carbomagnesiation of Alkynyl(aryl)thioethers†

  1. M. Sc. Thomas Kunz,
  2. Prof. Dr. Paul Knochel*

Article first published online: 17 JAN 2012

DOI: 10.1002/anie.201106734

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 8, pages 1958–1961, February 20, 2012

Additional Information

How to Cite

Kunz, T. and Knochel, P. (2012), Synthesis of Functionalized Benzo[b]thiophenes by the Intramolecular Copper-Catalyzed Carbomagnesiation of Alkynyl(aryl)thioethers. Angew. Chem. Int. Ed., 51: 1958–1961. doi: 10.1002/anie.201106734

Author Information

  1. Ludwig Maximilians-Universität München, Department Chemie, Butenandtstrasse 5–13, Haus F, 81377 München (Germany)

*Ludwig Maximilians-Universität München, Department Chemie, Butenandtstrasse 5–13, Haus F, 81377 München (Germany)

  1. †

    We thank the Fonds der Chemischen Industrie and the European Research Council (ERC) for financial support. We also thank BASF AG (Ludwigshafen) and Chemetall GmbH (Frankfurt) for generous gifts of chemicals.

Publication History

  1. Issue published online: 14 FEB 2012
  2. Article first published online: 17 JAN 2012
  3. Manuscript Revised: 25 NOV 2011
  4. Manuscript Received: 22 SEP 2011

Funded by

  • Fonds der Chemischen Industrie
  • European Research Council (ERC)

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Keywords:

  • benzo[b]thiophenes;
  • carbomagnesiation;
  • copper catalysis;
  • cyclization;
  • heterocycle synthesis
Thumbnail image of graphical abstract

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.

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