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Computational studies on CuAAC reaction mechanism with [CuX(PPh3)]; X = I, Br, Cl for the synthesis of 4- and 5-halo-1,2,3-triazoles

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Abstract

A complementary catalytic system was investigated for the [3 + 2] cycloaddition of azides and halo-alkynes. These are based on three copper complexes with [CuX (PPh3)]; X = I, Br, Cl, which are active at low metal loadings (the PPh3 system). The computational MN12-L approach showed acceptable results with levels of Def2-TZVPfor Cu and Def2-SVP for other elements. In general, all the computational results indicate that the cycloaddition reaction favors the formation of the observed 1,4-regioisomer (5-halo-triazoles) through a direct π-activation mechanism.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Tishreen University, Lattakia, Syrian Arab Republic

    Ali A. Khairbek & Mohammad Abd Al-Hakim Badawi

  2. Department of Chemistry, Faculty of Science & Arts, King Khalid University, Mohail, Assir, Saudi Arabia

    Abdullah Y. Alzahrani

  3. Department of Chemistry, St Berchmans College (Autonomous), Changanassery, Kerala, 686101, India

    Renjith Thomas

  4. Centre for Theoretical and Computational Chemistry, St Berchmans College (Autonomous), Changanassery, Kerala, 686101, India

    Renjith Thomas

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  1. Ali A. Khairbek
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Khairbek, A.A., Alzahrani, A.Y., Badawi, M.A.AH. et al. Computational studies on CuAAC reaction mechanism with [CuX(PPh3)]; X = I, Br, Cl for the synthesis of 4- and 5-halo-1,2,3-triazoles. Reac Kinet Mech Cat 137, 777–790 (2024). https://doi.org/10.1007/s11144-023-02548-z

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