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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, Email: laurent.micouinuniv-paris5.fr

B. Wang, M. Bonin, L. Micouin, Org. Lett., 2004, 6, 3481-3484.

DOI: 10.1021/ol048741i (free Supporting Information)


Abstract

A triethylamine-catalyzed metalation of terminal alkynes with trimethylaluminum (a readily available, inexpensive, and nontoxic metalating agent) gives alkynyldimethylaluminum reagents. These compounds react efficiently with various aromatic and heterocyclic halides in the presence of a palladium catalyst offering a simple entry to numerous internal alkynes.

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Key Words

Cross-Coupling, Alkynylation, Palladium Catalysis


ID: J54-Y2004-790