Palladium-Catalyzed Cross-Coupling of Aryl Electrophiles with Dimethylalkynylaluminum Reagents

Baomin Wang, Martine Bonin,* and Laurent Micouin*
Laboratoire de Chimie Thérapeutique, UMR 8638 associée au CNRS et à l'Université René Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4 av de l'Observatoire, 75270 Paris Cedex 06, France
Org. Lett., 2004, 6 (20), pp 3481–3484
DOI: 10.1021/ol048741i
Publication Date (Web): August 27, 2004
Copyright © 2004 American Chemical Society

Abstract

Abstract Image

Alkynyldimethylaluminum reagents are easily available from terminal akynes and trimethylaluminum via a triethylamine-catalyzed metalation. These compounds can react with various aromatic and heterocyclic halides in the presence of palladium in a fast and efficient way. This catalyzed cross-coupling reaction provides a simple entry to numerous internal alkynes, using a readily available, inexpensive, and nontoxic metalating agent.

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History

  • Published In Issue September 30, 2004
  • Received July 2, 2004

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