Novel Synthesis of 2-Oxo-3-butynoates by Copper-Catalyzed Cross-Coupling Reaction of Terminal Alkynes and Monooxalyl Chloride

Minjie Guo, Dao Li, and Zhaoguo Zhang*
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China zhaoguo@mail.sioc.ac.cn
J. Org. Chem., 2003, 68 (26), pp 10172–10174
DOI: 10.1021/jo0353076
Publication Date (Web): November 20, 2003
Copyright © 2003 American Chemical Society
*

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

Abstract

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A general and efficient Cu(I)-catalyzed cross-coupling reaction of terminal alkynes and monooxalyl chloride for the synthesis of 2-oxo-3-butynoates and 2-oxo-3-butynoamides was developed. Readily available starting materials, the mild reaction conditions, wide functional group tolerance, and the obviation of stoichiometric organolithium or magnesium reagents combine to highlight this reaction.

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History

  • Published In Issue December 26, 2003
  • Received September 5, 2003

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