Pd-Catalyzed Copper-Free Carbonylative Sonogashira Reaction of Aryl Iodides with Alkynes for the Synthesis of Alkynyl Ketones and Flavones by Using Water as a Solvent

Bo Liang,† Mengwei Huang,† Zejin You,† Zhengchang Xiong,† Kui Lu,† Reza Fathi,*‡ Jiahua Chen,*† and Zhen Yang*†‡
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Science, and Laboratory of Chemical Genetics, ShenZhen Graduate School, Peking University, Beijing, 100871, China, and VivoQuest, Inc., 711 Executive Boulevard, Valley Cottage, New York 10989 zyang@pku.edu.cn
J. Org. Chem., 2005, 70 (15), pp 6097–6100
DOI: 10.1021/jo050498t
Publication Date (Web): June 17, 2005
Copyright © 2005 American Chemical Society
†

 Peking University.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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‡

 VivoQuest, Inc.

Abstract

Abstract Image

The Pd-catalyzed copper-free carbonylative Sonogashira coupling reaction to synthesize alkynyl ketones from terminal alkynes and aryl iodides was achieved by using water as a solvent. The reaction was carried out at room temperature under balloon pressure of CO with Et3N as a base. The developed method was successfully applied to the synthesis of flavones.

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History

  • Published In Issue July 22, 2005
  • Received March 11, 2005

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