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Ligand-Free Synthesis of 1,4-Disubstituted-1,3-diynes by Iron/Copper Cocatalyzed Homocoupling of Terminal Alkynes

  1. Peipei Wang,
  2. Xiaoyan Liu,
  3. Songlin Zhang*

Article first published online: 11 DEC 2012

DOI: 10.1002/cjoc.201200878

Issue

Chinese Journal of Chemistry

Chinese Journal of Chemistry

Volume 31, Issue 2, pages 187–194, February, 2013

Additional Information

How to Cite

Wang, P., Liu, X. and Zhang, S. (2013), Ligand-Free Synthesis of 1,4-Disubstituted-1,3-diynes by Iron/Copper Cocatalyzed Homocoupling of Terminal Alkynes. Chin. J. Chem., 31: 187–194. doi: 10.1002/cjoc.201200878

Author Information

  1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science of Soochow University, Suzhou, Jiangsu 215123, China

*Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science of Soochow University, Suzhou, Jiangsu 215123, China, Tel.: 0086-0512-65880352; Fax: 0086-0512-65880352

Publication History

  1. Issue published online: 18 FEB 2013
  2. Article first published online: 11 DEC 2012
  3. Manuscript Accepted: 9 OCT 2012
  4. Manuscript Received: 3 SEP 2012

Funded by

  • the National Natural Science Foundation of China. Grant Number: 21072143
  • the Priority Academic Program Development of Jiangsu Higher Education Institutions

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Keywords:

  • catalysis;
  • copper;
  • iron;
  • 1,3-diyne;
  • ligand-free

Abstract

A simple and efficient protocol for Fe/Cu cocatalyzed oxidative homocoupling reaction of terminal alkynes to symmetrical 1,4-disubstituted-1,3-diynes was presented. The results showed that both CuBr and FeCl3 played crucial roles in the reaction. It is noteworthy that this protocol employs mild, efficient, aerobic and ligand free conditions. The alkynes, including aromatic, heteroaromatic and aliphatic alkynes, were transformed into the corresponding 1,3-diynes in good to excellent yields.

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