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Phosphine‐Free Palladium Catalytic System for the Selective Direct Arylation of Furans or Thiophenes bearing Alkenes and Inhibition of Heck‐Type Reaction
Author(s) -
Chen Lu,
Roger Julien,
Bruneau Christian,
Dixneuf Pierre H.,
Doucet Henri
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100193
Subject(s) - chemistry , palladium , potassium carbonate , catalysis , aryl , heck reaction , phosphine , organic chemistry , medicinal chemistry , combinatorial chemistry , alkyl
Abstract Palladium acetate associated to potassium carbonate as catalytic system has been found to efficiently catalyse the direct 5‐arylation of furans or thiophenes bearing enal, enone or acrylate functions at carbon C‐2, and to inhibit the Heck‐type reaction. The nature of the base is crucial to control the selectivity of the arylation. In the presence of electron‐deficient aryl bromides and potassium carbonate as the base, the direct arylation is favoured, whereas the use of potassium fluoride gave selectively the Heck‐type product, and tri‐ n ‐butylamine the reductive addition product.