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A Mild and Versatile Method for Palladium‐Catalyzed Cross‐Coupling of Aryl Halides in Water and Surfactants
Author(s) -
Arcadi Antonio,
Cerichelli Giorgio,
Chiarini Marco,
Correa Mariano,
Zorzan Daniel
Publication year - 2003
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.200300356
Subject(s) - chemistry , palladium , aryl , catalysis , halide , aqueous solution , aqueous medium , halogenation , coupling reaction , pulmonary surfactant , organic chemistry , amination , suzuki reaction , combinatorial chemistry , alkyl , biochemistry
Various aqueous surfactants proved to be excellent media for carrying out palladium‐catalyzed Suzuki−Miyaura cross‐coupling reactions under mild conditions. The dehalogenation side reaction, which is usually a drawback with the aqueous protocol, was not observed. The concentration of the surfactant in water played a pivotal role for the reaction outcome. Smooth cross‐coupling of iodoanisole and a variety of aryl bromides, including electron‐rich derivatives, with aryl boronic acids occurred at room temperature in high yields either with [Pd(PPh 3 ) 4 ] or Pd/C as catalyst. The water‐surfactant Pd/C system combines high activity under ambient conditions (air), easy separation and recyclability. Palladium acetate was found to be effective in cross‐coupling of the less reactive aryl chlorides at 100 °C. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)