Organic Letters 2002-06-13

Palladium-imidazolium carbene catalyzed Mizoroki-Heck coupling with aryl diazonium ions.

Merritt B Andrus, Chun Song, Jiuqing Zhang

Index: J. Org. Chem. 4 , 2079, (2002)

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Abstract

[reaction: see text] Catalyst formed from N,N-bis(2,6-diisopropylphenyl)dihydroimidazolium chloride and palladium(II) acetate (2 mol %) was used, without added base, to efficiently produce Heck coupled products with olefins and aryl diazonium tetrafluoroborate substrates. The reactions were performed at room temperature, giving product in 2-4 h with 80-90% yields for isolated materials. Diazonium ions, formed in situ directly from anilines, also couple under these conditions.