Issue 2, 2013
From the journal:

Green Chemistry

Solvent-free Huisgen cyclization using heterogeneous copper catalysts supported on chelate resins†

Yasunari Monguchi,*a   Kei Nozaki,a   Toshihide Maejima,a   Yutaka Shimoda,a   Yoshinari Sawama,a   Yoshiaki Kitamura,b   Yukio Kitadebc  and  Hironao Sajiki*a  

* Corresponding authors

a Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan
E-mail: sajiki@gifu-pu.ac.jp, monguchi@gifu-pu.ac.jp
Fax: +81 58 230 8109
Tel: +81 58 230 8109

b Laboratory of Molecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan

c United Graduate School of Drug Discovery and Medicinal Information Sciences, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan

Abstract

Copper catalysts supported on chelate resins bearing iminodiacetate moieties (DIAION CR11) or polyamine moieties (DIAION CR20) as chelating functional groups (12% Cu/CR11 and 7% Cu/CR20, respectively) were developed. 12% Cu/CR11 effectively catalyzed the Huisgen cycloaddition of mono-substituted alkynes to azides in the presence of triethylamine under totally solvent-free conditions to afford the corresponding 1,4-disubstituted 1,2,3-triazoles in excellent yields and in a completely regioselective manner. Furthermore, the Huisgen cycloaddition was found to effectively proceed without addition of triethylamine by the use of 7% Pd/CR20 as a catalyst.

Graphical abstract: Solvent-free Huisgen cyclization using heterogeneous copper catalysts supported on chelate resins

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Article information

DOI
https://doi.org/10.1039/C2GC36584G
Article type
Paper
Submitted
09 Oct 2012
Accepted
03 Dec 2012
First published
05 Dec 2012

Green Chem., 2013,15, 490-495

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Solvent-free Huisgen cyclization using heterogeneous copper catalysts supported on chelate resins

Y. Monguchi, K. Nozaki, T. Maejima, Y. Shimoda, Y. Sawama, Y. Kitamura, Y. Kitade and H. Sajiki, Green Chem., 2013, 15, 490 DOI: 10.1039/C2GC36584G

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