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Org Lett. 2004 Sep 30;6(20):3481-4. doi: 10.1021/ol048741i.

Palladium-catalyzed cross-coupling of aryl electrophiles with dimethylalkynylaluminum reagents.

Organic letters

Baomin Wang, Martine Bonin, Laurent Micouin

Affiliations

  1. 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.

PMID: 15387528 DOI: 10.1021/ol048741i

Abstract

[reaction: see text] Alkynyldimethylaluminum reagents are easily available from terminal alkynes 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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