This research was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC), the Merck Frosst Centre for Therapeutic Research, and the University of Toronto. We thank Dr. Valentina Aureggi for her intellectual contributions.
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Communication
Efficient Synthesis of Benzothiophenes by an Unusual Palladium-Catalyzed Vinylic C![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
S Coupling†
Article first published online: 18 AUG 2009
DOI: 10.1002/anie.200902843
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 48, Issue 38, pages 7064–7068, September 7, 2009
Additional Information
How to Cite
Bryan, C., Braunger, J. and Lautens, M. (2009), Efficient Synthesis of Benzothiophenes by an Unusual Palladium-Catalyzed Vinylic CS Coupling. Angewandte Chemie International Edition, 48: 7064–7068. doi: 10.1002/anie.200902843
- †
Publication History
- Issue published online: 1 SEP 2009
- Article first published online: 18 AUG 2009
- Manuscript Received: 27 MAY 2009
Funded by
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Merck Frosst Centre for Therapeutic Research
- University of Toronto
Keywords:
- cross-coupling;
- palladium;
- sulfur heterocycles;
- synthetic methods;
- tandem catalysis
Graphical Abstract
The simultaneous construction of a CS and a CC bond under catalytic conditions forms the basis of an efficient route to diversely functionalized benzothiophenes from gem-dihalovinyl thiophenols. The CC bond can be formed in this tandem catalytic process with an organoboron reagent as shown in the scheme (R1=H, Me, F, Cl, Br, OCH2O; R2=H, Me; R3=aryl, heteroaryl, alkenyl, alkyl), or by Heck or Sonogashira coupling with an alkene or alkyne.