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Mechanistic Insights into Copper(I)-Catalyzed Azide-Alkyne Cycloadditions using Continuous Flow Conditions

  1. Michael Fuchs1,
  2. Walter Goessler2,
  3. Christian Pilger3,
  4. C. Oliver Kappe1

Article first published online: 27 JAN 2010

DOI: 10.1002/adsc.200900726

Issue

Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

Volume 352, Issue 2-3, pages 323–328, February 15, 2010

Additional Information

How to Cite

Fuchs, M., Goessler, W., Pilger, C. and Kappe, C. O. (2010), Mechanistic Insights into Copper(I)-Catalyzed Azide-Alkyne Cycloadditions using Continuous Flow Conditions. Adv. Synth. Catal., 352: 323–328. doi: 10.1002/adsc.200900726

Author Information

  1. 1

    Christian Doppler Laboratory for Microwave Chemistry (CDLMC) and Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28, 8010 Graz, Austria, Fax: (+43)-(0)316-380-9840

  2. 2

    Institute of Chemistry, Analytical Chemistry, Karl-Franzens-University Graz, Universitätsplatz 1, 8010 Graz, Austria

  3. 3

    BASF SE, 67056 Ludwigshafen, Germany

Publication History

  1. Issue published online: 17 FEB 2010
  2. Article first published online: 27 JAN 2010
  3. Manuscript Revised: 3 DEC 2009
  4. Manuscript Received: 20 OCT 2009

Funded by

  • BASF AG
  • Christian Doppler Research Society (CDG)

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Keywords:

  • 1,3-dipolar cycloaddition;
  • click chemistry;
  • copper catalysis;
  • flow chemistry;
  • microwave chemistry;
  • 1,2,3-triazoles

Abstract

The copper-catalyzed azide-alkyne cycloaddition (CuAAC, “click chemistry”) was studied employing copper-in-charcoal (Cu/C) and a variety of copper metal sources as “heterogeneous” catalysts. The type and pretreatment conditions of the different copper sources on the CuAAC were investigated. In addition, the effect of copper leaching from the catalyst over time and in dependence on the reaction mixture composition was studied by ICP-MS analysis in the continuous flow mode. These investigations confirm a “homogeneous” mechanism and suggest surface layer copper(I) oxide as the catalytically active species in CuAAC chemistry involving zerovalent copper metal.

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