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Ultrasound Assisted High-Throughput Synthesis of 1,2,3-Triazoles Libraries: A New Strategy for “Click” Copper-Catalyzed Azide-Alkyne Cycloaddition Using Copper(I/II) as a Catalyst

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Abstract

A series of 1,4-disubstituted 1,2,3-triazoles were prepared by a parallel synthesis protocol utilizing the 3D-supramolecular coordination polymer (SCP) {[CuI(CN)(phen)2·CuII(CN)2(phen)]·5H2O}, 1 as a catalyst under ultrasonic irradiations. This work establishes the synergistic action between the mixed valance copper catalyst SCP 1 and ultrasonic irradiation to yield a high-throughput synthesis of 1,4-disubstituted 1,2,3-triazoles libraries. This mixed valance copper(I/II) supramolecular coordination polymer catalyzed azide alkyne cycloaddition reaction protocol allowed a rapid synthesis of the target compounds (10 min) in a parallel fashion with good to excellent yields. Twelve reactions were performed in a single deep well microtiter plate, employing three alkynes and four different azide reagents. From this effort, a total of twelve 1,2,3-triazole were obtained in useful isolated yields. Moreover, unambiguous structural assignment of the obtained regioisomers was determined utilizing Heteronuclear Multiple Bond Correlation (HMBC) 2D NMR techniques as a valuable.

Graphical Abstract

A series of 1,4-disubstituted 1,2,3-triazoles were prepared by a parallel synthesis protocol utilizing the 3D-supramolecular coordination polymer (SCP) {[CuI(CN)(phen)2·CuII(CN)2(phen)]·5H2O}, 1 as a catalyst under ultrasonic irradiations.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, University of Jeddah, P.O. Box 80329, Jeddah, 21589, Saudi Arabia

    Mohamed M. El-bendary, Tamer S. Saleh & Abdullah S. Al-Bogami

  2. Chemistry Department, Faculty of Science, Tanta University, Tanta, 31527, Egypt

    Mohamed M. El-bendary

  3. Green Chemistry Department, National Research Centre, El Buhouth St., Dokki, 12622, Cairo, Egypt

    Tamer S. Saleh

Authors
  1. Mohamed M. El-bendary
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  2. Tamer S. Saleh
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  3. Abdullah S. Al-Bogami
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Correspondence to Mohamed M. El-bendary or Tamer S. Saleh.

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El-bendary, M.M., Saleh, T.S. & Al-Bogami, A.S. Ultrasound Assisted High-Throughput Synthesis of 1,2,3-Triazoles Libraries: A New Strategy for “Click” Copper-Catalyzed Azide-Alkyne Cycloaddition Using Copper(I/II) as a Catalyst. Catal Lett 148, 3797–3810 (2018). https://doi.org/10.1007/s10562-018-2576-0

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