PAPER	Synthesis 2007: 1970-1978   DOI: 10.1055/s-2007-983729
© Georg Thieme Verlag Stuttgart · New York
The Surfactant-Promoted Cross-Coupling Reactions of Arylboronic Acids with Carboxylic Anhydrides or Acyl Chlorides in Water
Bingwei Xina,b, Yuhong Zhang*a, Kai Chenga
a Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China Fax: +86(571)87951512; e-Mail: yhzhang@zjuem.zju.edu.cn; b Department of Chemistry, Dezhou University, Dezhou 253023, P. R. of China
Received 19 March 2007

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