Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 26, Pages 5077-5088Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100480
Keywords
Palladium; Heterocycles; C-N coupling; Amination
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Funding
- Centre National de la Recherche Scientifique (CNRS)
- European Union (EU) within the EST network [MEST-CT-2005-020580]
- Region Ile-de-France
- l'Association pour la Recherche sur le Cancer (ARC)
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An efficient and general palladium-catalyzed coupling reaction between 3-bromocoumarins, 3-broinoquinolin-2(1H)-ones, and 3-iodo-2H-chromenes with a variety of nitrogen-containing nucleophiles (azole, amide, lactam, sulfonamide, aniline, amine, and urea) is described. The reaction proceeded rapidly and cleanly in dioxane providing the coupling products in good to excellent yields. The chemoselectivity of this reaction was also studied with polyhalocoumarins. Under optimized conditions, these underwent a site-selective amination at the C-3-Br bond, regardless of the nature of the nitrogen-containing nucleophile used.
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