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Palladium‐Catalyzed Direct Arylations of Five‐Membered Heteroarenes Bearing N ‐Monoalkylcarboxamide Substituents
Author(s) -
Laidaoui Nouria,
Roger Julien,
Miloudi Abdellah,
El Abed Douniazad,
Doucet Henri
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.201100312
Subject(s) - chemistry , substituent , palladium , aryl , thiophene , furan , nitrile , trifluoromethyl , pyrazole , medicinal chemistry , catalysis , pyrrole , bromide , amide , solvent , organic chemistry , alkyl
The palladium‐catalyzed direct arylation of furan, thiophene, pyrrole, or pyrazole derivatives bearing CONHR substituents on C2, C3, or C5 with aryl bromides was studied. The use of KOAc as the base, DMAc as the solvent, and PdCl(C 3 H 5 )(dppb) as the catalyst was found to give regioselectively and without decarbamoylation the arylated heteroaromatics. Under these conditions, the amide substituent on the heteroaromatic does not act as a directing group. A wide range of functional groups such as acetyl, formyl, ester, nitrile, trifluoromethyl, and fluoro on the aryl bromide is tolerated.