Full Paper

Copper-Catalyzed Cycloaddition of Sulfonyl Azides with Alkynes to Synthesize N-Sulfonyltriazoles ‘on Water’ at Room Temperature

  1. Feng Wang1,
  2. Hua Fu1,
  3. Yuyang Jiang1,2,
  4. Yufen Zhao1

Article first published online: 24 JUL 2008

DOI: 10.1002/adsc.200800291

Issue

Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

Volume 350, Issue 11-12, pages 1830–1834, August 4, 2008

Additional Information

How to Cite

Wang, F., Fu, H., Jiang, Y. and Zhao, Y. (2008), Copper-Catalyzed Cycloaddition of Sulfonyl Azides with Alkynes to Synthesize N-Sulfonyltriazoles ‘on Water’ at Room Temperature. Adv. Synth. Catal., 350: 1830–1834. doi: 10.1002/adsc.200800291

Author Information

  1. 1

    Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, People's Republic of China, Fax: (+86)-10-6278-1695

  2. 2

    Key Laboratory of Chemical Biology (Guangdong Province), Graduate School of Shenzhen, Tsinghua University, Shenzhen 518057, People's Republic of China

Publication History

  1. Issue published online: 31 JUL 2008
  2. Article first published online: 24 JUL 2008
  3. Manuscript Revised: 19 JUN 2008
  4. Manuscript Received: 12 MAY 2008

Funded by

  • National Natural Science Foundation of China. Grant Number: 20672065
  • Chinese 863 Project. Grant Number: 2007AA02Z160
  • Programs for New Century Excellent Talents in University. Grant Number: NCET-05–0062
  • Changjiang Scholars and Innovative Research Team in University (PCSIRT). Grant Number: IRT0404
  • Key Subject Foundation from Beijing Department of Education. Grant Number: XK100030514

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Keywords:

  • copper-catalyzed reaction;
  • on water;
  • S ligands;
  • sulfonyl azides;
  • N-sulfonyltriazoles

Abstract

We have developed a green and practical method for the Huisgen cycloaddition of water-insoluble sulfonyl azides with alkynes ‘on water’ at room temperature under catalysis of the inexpensive catalyst system CuX/PhSMe, and addition of the ligand (thioanisole) greatly inhibited cleavage of the N1[BOND]N2 bond in the 5-cuprated N-sulfonyltriazole intermediates to amides and improved the yields of N-sulfonyltriazoles.

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