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Palladium‐Catalyzed Coupling of 3‐Halo‐Substituted Coumarins, Chromenes, and Quinolones with Various Nitrogen‐Containing Nucleophiles
Author(s) -
Soussi Mohamed Ali,
Audisio Davide,
Messaoudi Samir,
Provot Olivier,
Brion JeanDaniel,
Alami Mouâd
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100480
Subject(s) - nucleophile , chemistry , chemoselectivity , amination , aniline , palladium , amide , azole , sulfonamide , organic chemistry , catalysis , amine gas treating , combinatorial chemistry , medicinal chemistry , antifungal , medicine , dermatology
An efficient and general palladium‐catalyzed coupling reaction between 3‐bromocoumarins, 3‐bromoquinolin‐2(1 H )‐ones, and 3‐iodo‐2 H ‐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.