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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Weir, Ron / Stohner, Jürgen

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Volume 80, Issue 5 (Jan 2008)

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Evaluation of catalytic activity of copper salts and their removal processes in the three-component coupling reactions

Seung Jun Hwang
  • Corresponding author
  • Center for Molecular Design and Synthesis (CMDS), Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701, Korea
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Seung Hwan Cho
  • Corresponding author
  • Center for Molecular Design and Synthesis (CMDS), Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701, Korea
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Sukbok Chang
  • Corresponding author
  • Center for Molecular Design and Synthesis (CMDS), Department of Chemistry and School of Molecular Science (BK21), Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701, Korea
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/pac200880050873

The catalytic activity of a wide range of copper salts, including Cu(I) and Cu(II), has been examined in the Cu-catalyzed three-component coupling reactions of sulfonyl azides, terminal alkynes, and amines, alcohols, or water to afford N-sulfonyl amidines, imidates, and amides, respectively. Furthermore, the investigation on the ligand effect in our protocol has revealed that certain types of ligands such as tris(benzyltriazolylmethyl)amine (TBTA) exhibited notable acceleration effects on the coupling reaction. The facile and efficient methods for removing copper salts from reaction mixture were also examined.

Keywords: amides; amidines; imidates; ligand effects; removal of copper salts; three-component reactions

Conference

International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14), International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis, OMCOS, Organometallic Chemistry Directed Toward Organic Synthesis, 14th, Nara, Japan, 2007-08-02–2007-08-06

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About the article

Published Online: 2009-01-01

Published in Print: 2008-01-01


Citation Information: Pure and Applied Chemistry, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac200880050873.

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