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Palladium Catalyzed Direct 3‐Arylation of Benzofurans using Low Catalyst Loadings
Author(s) -
Ionita Marina,
Roger Julien,
Doucet Henri
Publication year - 2010
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.200900258
Subject(s) - aryl , catalysis , chemistry , benzofuran , palladium , nitrile , trifluoromethyl , bromide , organic chemistry , hydroxymethyl , combinatorial chemistry , alkyl
The palladium‐catalyzed direct 3‐arylation of benzofurans provides a cost‐effective and environmentally attractive route for the preparation of 3‐arylbenzofuran derivatives. The reactions were carried out using a wide variety of electronically and sterically diverse aryl or heteroaryl bromides with low catalyst loadings. In the presence of only 0.1–0.5 mol % catalyst, products in moderate to good yields were obtained. The aryl bromide reactants were able to tolerate a wide range of functionalities, such as acetyl, propionyl, formyl, ester, nitrile, trifluoromethyl, or fluoro groups. Higher yields were obtained using electron‐deficient aryl bromides as reactants compared to using electron‐rich aryl bromides. Functionalized benzofuran derivatives, bearing formyl or hydroxymethyl on C2, were also successfully employed.