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CuI/l-proline catalyzed click reaction in glycerol for the synthesis of 1,2,3-triazoles

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Abstract Despite the apparent simplicity of the copper(I) iodide catalyzed CuAAC reaction, the conversion of the catalytic species, i.e. Cu(I) to thermodynamically more stable Cu(II), via aerial oxidation or disproportionation… Click to show full abstract

Abstract Despite the apparent simplicity of the copper(I) iodide catalyzed CuAAC reaction, the conversion of the catalytic species, i.e. Cu(I) to thermodynamically more stable Cu(II), via aerial oxidation or disproportionation is a major issue. To stabilize the Cu(I) species, the reaction is ideally carried out under an inert atmosphere in the presence of additives such as alcohols, amines, thiols, and aldehydes. Herein, we report the first CuI catalyzed click reaction without an inert atmosphere by employing the CuI/ l -proline system in glycerol. The method showed remarkable stability towards sensitive functional groups such as acetonides and 1,2,4-trioxanes.

Keywords: proline catalyzed; glycerol; reaction; catalyzed click; cui proline; click reaction

Journal Title: Tetrahedron Letters
Year Published: 2019

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