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Dual roles of substituted thiourea as reductant and ligand in CuAAC reaction

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Abstract A highly efficient catalytic system, CuSO 4 ·5H 2 O/1-(4-methoxyphenyl)-3-phenylthiourea, for the copper(I)-catalyzed azide–alkyne cycloaddition reaction (CuAAC) was discovered. In the above catalytic system, substituted thiourea acts both as… Click to show full abstract

Abstract A highly efficient catalytic system, CuSO 4 ·5H 2 O/1-(4-methoxyphenyl)-3-phenylthiourea, for the copper(I)-catalyzed azide–alkyne cycloaddition reaction (CuAAC) was discovered. In the above catalytic system, substituted thiourea acts both as a reductant and a ligand. CuSO 4 ·5H 2 O/1-(4-methoxyphenyl)-3-phenylthiourea is both an economical and efficient catalyst for the CuAAC reaction. In addition, the new catalytic system has advantageous features including mild and green reaction conditions, and broad substrate compatibility. A variety of 1,4-disubstituted 1,2,3-triazoles have been prepared with good to excellent yields with the CuSO 4 ·5H 2 O/1-(4-methoxyphenyl)-3-phenylthiourea catalytic system in aqueous solution.

Keywords: cuaac; substituted thiourea; cuaac reaction; catalytic system; reaction; reductant ligand

Journal Title: Tetrahedron Letters
Year Published: 2017

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