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DABCO/AcOH Jointly Accelerated Copper(I)-Catalysed Cycloaddition of Azides and Alkynes on Water at Room Temperature

Prashant B. Sarode, Sandeep P. Bahekar, Hemant S. Chandak*

*Department of Chemistry, G. S. Science, Arts and Commerce College, Khamgaon 444303, India, Email: hschandakgsck.ac.in

P. B. Sarode, S. P. Bahekar, H. S. Chandak, Synlett, 2016, 27, 2681-2684.

DOI: 10.1055/s-0036-1588590 (free Supporting Information)


Abstract

A combination of CuSO4-ascorbate/1,4-diazabicyclo[2.2.2]octane/acetic acid enables an expeditious room temperature synthesis of 1,4-disubstituted 1,2,3-triazoles from terminal alkynes and various azides, such as aryl, alkyl, and sulfonyl azides. Acetic acid accelerates the protonation of cuprated triazole and thus avoids possible side reactions. Devoid of acetic acid, the reaction pathway results in the formation of sulfonamides.

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Key Words

CuAAC, DABCO, alkynes, azides, 1,2,3-triazoles


ID: J60-Y2016