Phosphine-Free Cross-Coupling Reaction of Arylboronic Acids with Carboxylic Anhydrides or Acyl Chlorides in Aqueous Media

Bingwei Xin,†‡ Yuhong Zhang,*† and Kai Cheng†
Department of Chemistry, Zhejiang University, Hangzhou 310027, P.R. China, and Department of Chemistry, Dezhou University, Dezhou 253023, P.R. China
J. Org. Chem., 2006, 71 (15), pp 5725–5731
DOI: 10.1021/jo060749d
Publication Date (Web): June 21, 2006
Copyright © 2006 American Chemical Society
†

 Zhejiang University.

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‡

 Dezhou University.

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*

 Corresponding author. Phone:  +86-571-87953253. Fax:  +86-571-87951512.

, yhzhang@zjuem.zju.edu.cn

Abstract

Abstract Image

The palladium acetate-catalyzed coupling reaction of aryl boronic acid with carboxylic anhydride or acyl chloride was carried out smoothly in water in the presence of poly(ethylene glycol) (PEG) or 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]) to give high yields of ketones without the use of phosphine ligands. The Pd(OAc)2−H2O−[bmim][PF6] catalytic system can be recovered and reused eight times with high efficiency for both carboxylic anhydride and acyl chloride.

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History

  • Published In Issue July 21, 2006
  • Received April 10, 2006

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