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Synthesis 2007(13): 1970-1978
DOI: 10.1055/s-2007-983729
DOI: 10.1055/s-2007-983729
PAPER
© Georg Thieme Verlag Stuttgart · New York
The Surfactant-Promoted Cross-Coupling Reactions of Arylboronic Acids with Carboxylic Anhydrides or Acyl Chlorides in Water
Further Information
Received
19 March 2007
Publication Date:
18 June 2007 (online)
Publication History
Publication Date:
18 June 2007 (online)
Abstract
The palladium(II) chloride catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides in water in the presence of various surfactants is described. The inexpensive and industrially widely used sodium dodecyl sulfate (SDS) was found to be a good promoter of the coupling reaction and aryl ketones were obtained in good yields without the use of phosphine ligands. The reactions were unaffected by the presence of electron-releasing and electron-withdrawing substituents in both the arylboronic acids and carboxylic derivatives and a variety of aryl ketones were obtained under mild conditions in air.
Key words
aryl ketone - boronic acid - carboxylic anhydride - acyl chloride - palladium catalysis
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